Method for controlling or inhibiting plant pathogenic bacteria

Abstract

The present invention relates to the use of N-methoxy(phenylethyl)-pyrazole carboxamides for controlling or inhibiting phytopathogenic bacteria; 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 (fluazumamide) for controlling or inhibiting phytopathogenic bacteria; and the use of compositions comprising such a compound.

Description

[0001] This invention relates to the use of N-methoxy(phenylethyl)-pyrazole carboxamide for controlling or inhibiting plant pathogenic bacteria; and compositions comprising such compounds. In particular, this 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 (fluopyram) for controlling or inhibiting plant pathogenic bacteria; and compositions comprising such compounds.

[0002] Bacterial plant diseases caused by plant pathogenic bacteria are a major concern for growers worldwide. These diseases often lead to hormonal imbalances in infected plants, which can result in problems such as stunted growth, excessive growth, galls, root branching, leaf drop, resetting, necrosis, tissue infiltration, wilting, reduced photosynthetic area, malformed growth, and apical dominance. These problems alter the nutritional levels of affected plants both qualitatively and quantitatively; furthermore, they negatively impact global food supplies and the economy. See Kannan et al., “Sustainable Approaches to Controlling Plant Pathogenic Bacteria”.

[0003] Plant pathogenic bacteria can be easily spread through a variety of means, including water, wind, insects, animals, human activities, agricultural and farming equipment (especially during the vegetative propagation of plants in nurseries), and can also be spread through the soil.

[0004] Controlling or inhibiting plant pathogenic bacteria is primarily achieved through the prevention and elimination of plant pathogens. Currently, solutions for controlling or inhibiting the activity of plant pathogenic bacteria on plants are limited. Major chemical controls include copper-based products (which often leave residues), agricultural antibiotics, and the use of resistance inducers such as aramid-benzene-S-methyl. Some fungicides used to control fungal diseases can have inhibitory effects on the diseases, even if they do not have a direct effect on the plant pathogenic bacteria themselves. For example, some methoxyacrylate fungicides can have a beneficial effect on plants and induce a defensive response; however, these usually require multiple applications and do not have a direct effect on the plant pathogenic bacteria themselves.

[0005] Compound 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide (fluopyram) 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 succinate dehydrogenase inhibitor (SDHI) class. This invention is based on the unexpected 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 effects, and thus can now be used against plant pathogenic bacteria and therefore against plant bacterial diseases.

[0006] Therefore, in a first aspect, the present invention relates to a method for controlling or inhibiting plant pathogenic bacteria on useful plants, the method 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 a plant, a plant part or the site thereof.

[0007] On the other hand, a method for controlling or inhibiting plant pathogenic bacteria on useful plants is provided, the method comprising applying an effective amount of a composition comprising 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichlorophenyl)ethyl]-1H-pyrazole-4-carboxamide to a plant, a plant part or the site thereof.

[0008] In another aspect, 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, diastereomer, enantiomer or tautomer thereof, for the control of bacterial diseases of plants is provided.

[0009] A method for controlling or inhibiting the effects of plant pathogenic bacteria on beneficial plants is also provided, the method 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 a plant, a plant part or the site thereof.

[0010] Another method is provided for controlling or inhibiting the effects of plant pathogenic bacteria on beneficial plants, the method comprising applying an effective amount of a composition comprising 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichlorophenyl)ethyl]-1H-pyrazole-4-carboxamide to a plant, a plant part or the site thereof.

[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-trichlorophenyl)ethyl]-1H-pyrazole-4-carboxamide exists in two enantiomers: 3-(difluoromethyl)-N-methoxy-1-methyl-N-[(1R)-1-methyl-2-(2,4,6-trichlorophenyl)ethyl]-1H-pyrazole-4-carboxamide and 3-(difluoromethyl)-N-methoxy-1-methyl-N-[(1S)-1-methyl-2-(2,4,6-trichlorophenyl)ethyl]-1H-pyrazole-4-carboxamide. Both enantiomers can be used alone or as racemates to control or inhibit plant pathogenic bacteria. The compound 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide may be referred to herein by its full name, ISO name or as “compound”.

[0012] As described herein, the present invention relates to methods for controlling or inhibiting plant pathogenic bacteria on useful plants, methods comprising applying 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichlorophenyl)ethyl]-1H-pyrazole-4-carboxamide in an effective amount to the useful plant to be protected, or to the site thereof, to act on the plant pathogenic bacteria. 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichlorophenyl)ethyl]-1H-pyrazole-4-carboxamide may also be applied to plant propagation material, such as seeds, cuttings, and young plants.

[0013] A method for controlling or inhibiting the effects of plant pathogenic bacteria on beneficial plants is also described, comprising applying 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichlorophenyl)ethyl]-1H-pyrazole-4-carboxamide in an effective amount to the beneficial plant to be protected, or to the site thereof, to act on the plant pathogenic bacteria.

[0014] As used herein, the term "useful plants" typically includes plants of the following species: grapevines; cereals such as wheat, barley, rye, or oats; beets such as sugar beets or forage beets; fruits such as pome, drupe, 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 crops such as rapeseed, mustard, poppies, olives, sunflowers, coconuts, castor oil plants, cocoa beans, or peanuts; cucurbitaceous plants such as zucchini, cucumbers, or cantaloupes; fiber plants such as cotton, flax, hemp, or jute; and citrus aquatic plants. Fruits, such as oranges, lemons, grapefruits, or tangerines; vegetables, such as brassicasae, spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, sweet potatoes, gourds, peppers, chilies, or herbs; Lauraceae, such as avocados, cinnamon, or camphor; rice; corn; tobacco; nuts; coffee; sugarcane; tea; vines; hops; durian; bananas; natural rubber plants; turf or ornamental plants, such as flowering plants, shrubs, broad-leaved trees, or evergreens, such as conifers; ornamental crops, such as roses, geraniums, geraniums, impatiens, cyclamen, poinsettias, pansies, magnolias, or zinnias; bulbous flowers, such as tulips. The above list does not constitute any limitation.

[0015] As used in this article, the term "plant pathogenic bacteria" refers to bacteria that cause plant diseases. 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., *Pectobacterium* spp., *Phytoplasma* spp., *Pseudomonas* spp., and *Ralstonia* spp. The genera *Rhizobacter*, *Rhizomonas*, *Rhodococcus*, *Serratia*, *Sphingomonas*, *Sprioplasma*, *Streptomycess*, *Xanthomonas*, and *Xylella* are listed as spp.

[0016] As used herein, the term "site" means the place in which or on which a plant grows, or the place where the seeds of a cultivated plant are sown, or the place where the seeds will be placed in the soil. It includes soil, seeds, and seedlings, along with the established vegetation.

[0017] The term "plant" refers to all the tangible parts of a plant, including seeds, seedlings, roots, stems, culms, and leaves.

[0018] As used herein, the term "plant propagation material" should be understood to refer to the reproductive parts of a useful plant, such as seeds, which can be used for the propagation of that useful plant, as well as nutrient materials, such as cuttings or tubers (e.g., potatoes). References may include, for example, seeds (in the strict sense), roots, fruits, tubers, bulbs, corms, rhizomes, and plant parts. References may also include germinating plants and young plants to be transplanted after germination or emergence. These young plants may be protected prior to transplanting by complete or partial treatment with a compound. Preferably, "plant propagation material" should be understood to refer to seeds and / or roots, more preferably seeds.

[0019] As used herein, the term "bactericide" for 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 pathogenic bacteria.

[0020] To control or inhibit plant pathogenic bacteria, 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichlorophenyl)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-trichlorophenyl)ethyl]-1H-pyrazole-4-carboxamide that, when applied appropriately, is sufficient to achieve the desired level of control or inhibition of plant pathogenic bacteria.

[0021] For example, in the case of Xanthomonas, the efficacy of 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichlorophenyl)ethyl]-1H-pyrazole-4-carboxamide against plant pathogenic bacteria can be assessed by comparing the area of ​​affected leaves. Technicians are familiar with such methods, and further details of various methods are given in the following examples.

[0022] As used herein, the phrase “control or inhibit the effects of plant pathogenic bacteria” for 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichlorophenyl)ethyl]-1H-pyrazole-4-carboxamide means that the compound can reduce the incidence or severity of the effects of plant pathogenic bacteria on beneficial plant crops. For example, in the case of Xanthomonas, it prevents or reduces leaf spot; and in the case of Agrobacterium, it prevents galls (i.e., prevents tumor formation). This list does not represent any limitation.

[0023] The compound 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichlorophenyl)ethyl]-1H-pyrazole-4-carboxamide can be used to maintain plant health and can be used to therapeutically, preventively, or systematically control or inhibit plant pathogenic bacteria. Controlling or inhibiting plant pathogenic bacteria reduces damage to plants and can therefore correspondingly increase yield.

[0024] Examples of plant pathogenic bacteria 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*, *Acidobacterium*, *Arthrobacter*, *Burkholderia*, *Bacillus phloem*, *Corynebacterium*, *Clostridium*, *Corynebacterium*, *Dichotomyces*, *Erwinia*, *Rifampia*, *Pantotheca*, *Fructus*, *Fructus*, *Phytoplasma*, *Pseudomonas*, *Ralstonia*, *Rhizobium*, *Serratia*, *Sphingomonas*, *Spiroplasma*, *Streptomyces*, *Xanthomonas*, and *Trichobacter*.

[0025] In particular, examples of plant pathogenic bacteria to which 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-yl)ethyl]-1H-pyrazole-4-carboxamide can be applied include Agrobacterium, Bacillus phloem, Corynebacterium, Dichotomyces, Erwinia, Fruit Bacillus, Pseudomonas, Larstonia, and Xanthomonas.

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

[0027] More preferably, the plant pathogenic bacteria to which 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichlorophenyl)ethyl]-1H-pyrazole-4-carboxamide can be applied include *Agrobacterium tumefaciens*, *Potamogeton crispus*, *Potamogeton black shank*, *Pyrostemum purpureum*, *Pectinobacterium tumefaciens*, *Ralstonia solanaceae*, *Xanthomonas rubrum*, *Xanthomonas oryzae*, *Xanthomonas oryzae*, *Xanthomonas oryzae*, *Xanthomonas perforatum*, and *Streptomyces hygroscopicus*.

[0028] In one embodiment, a method is provided for controlling or inhibiting plant pathogenic bacteria selected from the following: Xanthomonas, Pseudomonas, Agrobacterium, Larstonia, Corynebacterium, and Trichoderma. A method is also provided for controlling or inhibiting the effects of plant pathogenic bacteria on beneficial plants, wherein the plant pathogenic bacteria are selected from Xanthomonas, Pseudomonas, Agrobacterium, Larstonia, Corynebacterium, and Trichoderma.

[0029] In another embodiment, a method is provided for controlling or inhibiting plant pathogenic bacteria selected from the genera *Agrobacterium*, *Pseudomonas*, *Ralstonia*, and *Xanthomonas*. A method is also provided for controlling or inhibiting the effects of plant pathogenic bacteria on beneficial plants, wherein the plant pathogenic bacteria are selected from the genera *Agrobacterium*, *Pseudomonas*, *Ralstonia*, and *Xanthomonas*.

[0030] As shown in this article, 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichlorophenyl)ethyl]-1H-pyrazole-4-carboxamide is effective against *Agrobacterium*, *Pseudomonas syringae*, *Ralstonia*, and *Xanthomonas*. In particular, 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichlorophenyl)ethyl]-1H-pyrazole-4-carboxamide is especially effective against *Agrobacterium tumefaciens*, *Pseudomonas syringae*, *Xanthomonas perforatum*, *Xanthomonas oryzae*, and *Xanthomonas spp.*

[0031] Useful plants for 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichlorophenyl)ethyl]-1H-pyrazole-4-carboxamide include grapevines; cereals such as wheat, barley, rye, or oats; beets such as sugar beets or forage beets; fruits such as pome, stone fruit, or soft fruit, such as apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, or blackberries; legumes such as beans, lentils, peas, or soybeans; oil crops such as rapeseed, mustard, poppies, olives, sunflowers, coconuts, castor oil plants, cocoa beans, or peanuts; cucurbitaceous plants such as zucchini, cucumbers, or cantaloupes; and fiber plants. Such as cotton, flax, hemp, or jute; citrus fruits such as oranges, lemons, grapefruits, or tangerines; vegetables such as brassicas, spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, sweet potatoes, gourds, peppers, chilies, or herbs; Lauraceae, such as avocados, cinnamon, or camphor; rice; corn; tobacco; nuts; coffee; sugarcane; tea; vines; hops; durian; bananas; natural rubber plants; turf or ornamental plants such as flowers, shrubs, broad-leaved trees, or evergreens, such as pines and cypresses; ornamental crops such as roses, geraniums, geraniums, impatiens, cyclamen, poinsettias, pansies, magnolias, and zinnias; bulbous flowers such as tulips.

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

[0033] The compound 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichlorophenyl)ethyl]-1H-pyrazole-4-carboxamide, used for controlling plant pathogenic bacteria, can be used in unmodified form, or preferably in combination with carriers and adjuvants conventionally used in the field of formulations, and as previously described in WO 2010 / 063700. Typically, when used for fungal control, 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichlorophenyl)ethyl]-1H-pyrazole-4-carboxamide is applied to the beneficial plant by foliar application. However, for controlling plant pathogenic bacteria, the preferred method of application is direct application to the plant, the plant site (e.g., soil), or direct application to plant propagation material (e.g., to seeds).

[0034] In another embodiment, 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichlorophenyl)ethyl]-1H-pyrazole-4-carboxamide is applied to plants, plant parts, or the site thereof in the form of a bactericidal formulation. This formulation may contain one or more other desired components, including but not limited to liquid diluents, binders acting as a matrix for compounds as described herein, fillers for protecting seeds, and plasticizers for improving the flexibility, adhesion, and / or spreadability of the coating.

[0035] Antibacterial formulations, such as compositions containing 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichlorophenyl)ethyl]-1H-pyrazole-4-carboxamide 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 a compensator (e.g., a solvent, a solid carrier, and optionally a surfactant compound).

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

[0037] The compositions of the present invention can be used in any conventional form, such as in the form of double-packaged powders for dry seed treatment (DS), emulsions for seed treatment (ES), flowable concentrates for seed treatment (FS), solutions for seed treatment (LS), water-dispersible powders for seed treatment (WS), capsule suspensions for seed treatment (CF), gels for seed treatment (GF), emulsion concentrates (EC), suspension concentrates (SC), suspension emulsions (SE), capsule suspensions (CS), water-dispersible particles (WG), emulsifiable particles (EG), water-in-oil emulsions (EO), oil-in-water emulsions (EW), microemulsions (ME), dispersible oil suspensions (OD), oil suspensions (OF), oil-soluble liquids (OL), soluble concentrates (SL), ultra-low volume suspensions (SU), ultra-low volume liquids (UL), technical grade (TK), dispersible concentrates (DC), wettable powders (WP), or any technically feasible formulations in combination with agriculturally acceptable adjuvants.

[0038] Such compositions can be produced in conventional ways, for example by mixing the active ingredient with appropriate formulation inert agents (diluents, solvents, fillers, and optionally other formulation components such as surfactants, biocides, antifreeze agents, adhesives, thickeners, and compounds that provide auxiliary effects). Conventional sustained-release formulations designed for long-term sustained efficacy can also be used. In particular, formulations intended for application in 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 that provide auxiliary effects, such as condensations of formaldehyde with naphthalene sulfonates, alkylaryl sulfonates, lignin sulfonates, fatty alkyl sulfates, and ethoxylated alkylphenols and ethoxylated fatty alcohols.

[0039] Typically, formulations comprise from 0.01% to 90% by weight of an active agent, from 0% to 20% of an agriculturally acceptable surfactant, and from 10% to 99.99% of a solid or liquid formulation inert agent and one or more adjuvants. The active agent is composed of at least 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichlorophenyl)ethyl]-1H-pyrazole-4-carboxamide together with components (B) and (C), and optionally other active agents (particularly microbicides, preservatives, or the like). Concentrated forms of the composition typically contain between about 2% and 80% by weight of the active agent, preferably between about 5% and 70%. Application forms of the formulation may, for example, contain from 0.01% to 20% by weight of the active agent, preferably from 0.01% to 5% by weight. However, commercially available products are preferably formulated as concentrates, and end users will typically use 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 sole active ingredient in the composition, or, where appropriate, it may be mixed with one or more other active ingredients (such as pest control agents, fungicides, synergists, herbicides, or plant growth regulators). In some cases, the additional active ingredients may produce unexpected synergistic activity.

[0041] Examples of suitable other 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, acetamiprid, thiamethoxam, cypermethrin, phosmet, phosmet oxalate, amitraz, dicofol, arsenic trioxide, azobenzene, azophos, benomyl, benzoxazophos, benzyl oxalate, benzyl... Benzyl formate, bifenthrin, bromopyrrolizamide, bromofenoxam, bromothion, bromodiphenyl ether, thiamethoxam, methyl ethyl ketone, methyl ethyl sulfone, butylpyridaben, calcium polysulfide, camphene, chlorfenapyr, trithion, acaricide, dicofol, acaricide, acaricide hydrochloride, dicofol, dicofol, difenoconazole, ethyl dicofol, chloromebuform, diflubenzuron, propyl dicofol, chlorpyrifos, fenpropathrin I, fenpropathrin II, fenpropathrin, cloxacillin, phosmet, cloxacillin Ammonium phosphate, phosmet, thiophanate-methyl, phosmet, DCPM, DDT, phosmet-O, ​​phosmet-S, demeton-S-methylsulfon, phosmet, dichlorvos, dichlorvos, chlorpyrifos, fenflurphos, dinex, dinex-diclexine Acaricide-4, Acaricide-6, O-dimethoate, Ammonium nitrate, Oxyl nitrate, Butyl nitrate, Dichlorvos, Sulfonated diphenyl, Disulfiram, DNOC, Dofenapyn, Dofenapyn, Indomethacin, Irinocinolone, Ethiophos, Ethiophos, Acaricide, Benzocarb, Fenpyrad, Azoxystrobin, Acaricide, Fentrifanil, Flufenoxuron, Flufenoxuron, Bifenthrin, Flufenoxuron, FMC 1137, chlorfenapyr, chlorfenapyr hydrochloride, formocarb, γ-HCH, chlorfenapyr, benzoyl permethrin, hexadecylcyclopropane carboxylate, methamidophos, jasmine ester I, jasmine ester II, iodophos, lindane, propiconazole, pymetrozine, dithiamethoxam, methamidophos, chlorfenapyr, methyl bromide, methamidophos, milbemime, propanil, phorate, malathion, moxifloxacin, dibromophos (naled), 4-chloro-2-(2-chloro-2-methyl- Propyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazin-3-one, flufenoxuron, nicotinic acid, cyancarb, cyancarb 1:1 zinc chloride complex, omethoate, sulfoxide, sulfone phosmet, pp'-DDT, parathion, permethrin, fenthion, phosmet, thiocyclam, phosphamidon, polychloroterpenes, polynactins, prochloraz, carbendazim, propoxur, ethazolium, phosmetPyrethroid I, Pyrethroid II, Pyrethroid, Pyridaben, Pyrimethanil, Quinalphos, Quintiofos, R-1492, Glyphosate, Rotenone, Acephate, Ketoconazole, Slachlor, Thiophanate, SSI-121, Sufil, Fipronil, Thioteprazole, Sulfur, Flufenoxam, T-flufenoxam, TEPP, Terbufos, Tetrachlor, Acaricide, Thiafenoxam, Carbofuran, Dimethoate, Acaricide, Bacillus, Benomyl, Triazophos, Triazuron, Trichloropropoxyfen, Trichlorfon, Vaniliprole, Bethoxazin, Copper dioctanoate, Sulfuric acid, Ciprofloxacin yne), dichloronaphthoquinone, dichlorophenol, cypermethrin, triphenyltin, quicklime, sodium mancozeb, quinone, simazine, triphenyltin acetate, triphenyltin hydroxide, phosmet, piperazine, thiophanate-methyl, chloralose, fenthion, pyridine-4-amine, strychnine, 1-hydroxy-1H-pyridine-2-thione, 4-(quinoxalo-2-ylamino)benzenesulfonamide, 8-hydroxyquinoline sulfate, bromonitol, copper hydroxide, cresol, dipyrithione, dodexamethasone, sodium dichloroisocyanurate, formaldehyde, mercuroquinone, kasugamycin, kasugamycin hydrochloride hydrate, di(dimethyldithiocarbamate)nickel, trichloromethylpyridine, octathione, oxoryl acid, oxytetracycline, potassium hydroxyquinoline sulfate, thiabendazole, streptomycin, streptomycin sesquisulfate, thimerosal, cotton brown belt moth GV, *Agrobacterium radiata*, species of *Amblyseius* spp.), Celery noctuid moth NPV, *Anagrus atomus*, *Aphelinus abdominalis*, cotton aphid parasitic wasp, *Aphidoletes aphidimyza*, alfalfa silver-striped noctuid moth NPV, *Bacillus sphaericus Neide*, *Beauveria brongniartii*, common lacewing (*Chrysoperla carnea*), *Cryptolaemus montrouzieri*, codling moth GV, *Dacnus asibirica*, pea leafminer fly pygmy wasp (*Diglyphus isaea*), *Encarsia formosa*, *Eretmocerus eremicus*, *Heterorhabditis* bacteriophora and H. megidisThe following species were included: *Hippodamia convergens*, *Leptomastix dactylopii*, *Macrolophus caliginosus*, *Cabbage moth* NPV, *Metaphycus helvolus*, *Metarhizium anisopliae var. acridum*, *Metarhizium anisopliae var. anisopliae*, *Neodiprionsertifer* NPV and *N. lecontei* NPV, *Symplocos spp.* species, *Paecilomyces fumosoroseus*, *Phytoseiulus persimilis*, *Steinernema bibionis*, and *Steinernema* nematode. carpocapsae), Steinernema glaseri, Steinernema riobrave, Steinernema riobravis, Steinernema scapterisci, species of Steinernemaspp., species of Trichogramma, Typhlodromus occidentalis, Verticillium lecanii, apholate, bisazir, busulfan, dimatif, hemel, hempa, metepa, methiotepa, methyl pyrazophosphorus apholate), morzid, penfluron, tepa, thiohempa, thiotepa, tratamine, urethaneimine, (E)-dec-5-en-1-yl acetate and (E)-dec-5-en-1-ol, (E)-tetrate-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)-eicosero-13-en-10-one(Z)-Tetradecano-7-en-1-al, (Z)-Tetradecano-9-en-1-ol, (Z)-Tetradecano-9-en-1-yl acetate, (7E,9Z)-Dodeca-7,9-dien-1-yl acetate, (9Z,11E)-Tetradecano-9,11-dien-1-yl acetate, (9Z,12E)-Tetradecano-9,12-dien-1-yl acetate, 14-Methyloctadecano-1-ene, 4-Methylnon-5-ol and 4-Methylnon-5-one, α-polystyrene, western pine bark beetle pheromone, dodecadienol (codlelure), codlemone, cuelure, nonadecane oxide, dodecano-8-en-1-yl acetate, dodecano-9-en-1-yl acetate Ester, 10-dien-1-yl acetate, dodecylure, ethyl 4-methyloctanoate, eugenol, frontalin (a pheromone associated with the southern pine bark beetle), grandlure (a mixture of attractants), acetylene attractant I, acetylene attractant II, acetylene attractant III, acetylene attractant IV, hexalure, ipsdienol (a dienol associated with the tooth beetle), ipsenol (a dienol associated with the small beetle), japonilure (a pheromone associated with the scarab beetle), lineatin (a trimethyldioxane associated with the lineatin), litlure (a pheromone associated with the noctuid moth), looplure (a pheromone associated with the pink striped noctuid moth), medlure (a pheromone associated with the montmorillonite moth), megatomoic acid (a pheromone associated with the montmorillonite moth). (The following are listed as unrelated keywords and phrases: acid), methyleugenol, muscalure, octadec-2,13-dien-1-yl acetate, octadec-3,13-dien-1-yl acetate, orfralure, oryctalure, ostramone, siglure, sordidin, sulcatol, tetradec-11-en-1-yl acetate, trimedlure, Mediterranean fruit fly attractant A, Mediterranean fruit fly attractant B1, Mediterranean fruit fly attractant B2, Mediterranean fruit fly attractant C, trunc-call, 2-(octylthio)ethanol, butopyronoxyl, butoxy (polypropylene glycol), dibutyl adipate, dibutyl phthalate, dibutyl succinate, DEET, dimethyl methacrylate, etc.) Carbate, dimethyl phthalate, ethylhexanediol, hexamide, methoquin-butyl, methylneodecanamide, oxamate, picaridin1-Dichloro-1-nitroethane, 1,1-dichloro-2,2-di(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-ethylsulfinylethylmethyl phosphate, 2-(1,3-dithiopentane-2-yl)phenyldimethylcarbamate, 2-(2-butoxyethoxy)ethyl thiocyanate, 2-(4,5-dimethyl-1,3-dioxolane-2-yl)phenylmethylcarbamate Ester, 2-(4-chloro-3,5-dimethyloxy)ethanol, 2-chlorovinyl diethyl phosphate, 2-imidazolinone, 2-isovaleryl indan-1,3-dione, 2-methyl(prop-2-ynyl)aminophenyl methyl carbamate, 2-cyanothioethyl laurate, 3-bromo-1-chloroprop-1-ene, 3-methyl-1-phenylpyrazole-5-yl dimethyl carbamate, 4-methyl(prop-2-ynyl)amino-3,5-dimethylmethyl carbamate, 5,5-dimethyl-3-oxocyclohex-1-enyl dimethyl carbamate, asethio Phosphorus, Acrylonitrile, Chlorpyrifos, Aloxane, Carbendazim, Aloxane, Aluminum Phosphide, Methionine, Neonicotinamide, Athidathion, Methylpyridinium Phosphate, Bacillus thuringiensis δ-endotoxin, Barium Hexafluorosilicate, Barium Polysulfide, Cypermethrin, Bayer 22 / 190, Bayer 22408, β-Cypermethrin, β-Cypermethrin, Bioethanomethrin, Bis(2-chloroethyl) ether, Borax, Bromobenzenephos, Bromo-DDT, Carbendazim, Carbendazim, Specimens (b) Utathiofos), butyl phosphate, calcium arsenate, calcium cyanide, carbon disulfide, carbon tetrachloride, batan hydrochloride, cevadine, borneol, chlordane, decachlorophenone, chloroform, chloropicrin, chlorpyrifos, chlorpyrifos, cis-resmethri, cismethrin, clocythrin, copper acetylacetonate, copper arsenate, copper oleate, coumithoate, cryolite, CS 708, Benzoate, Phytazonium, Cypermethrin, Phytophos, d-methoxyfenozide, DAEP, Dazomet, Decarbofuran, Diamidafos, Isochlor, Phytophos, Dicrylonitrile, Cypermethrin, Diethyl-5-methylpyrazol-3-yl phosphate, Dior, Tetrafluoromethrin, Dimethoate, Permethrin, Methylpyridaben, Difenoconazole, Propnitrophenol, Pendimethalin, Diphenoxyphenoxyacetic acid, Benzylphos, Phenylephrine, Fipronil, Thiamethoxam, DSP, Ecdysterone, EI 1642, EMPC, EPBP, Etaphos, EthylbenzylcarbamateEthyl formate, dibromoethane, dichloroethane, ethylene oxide, EXD, phosmet, ethylcarbide, fenitrothion, fenoxacrim, pyrethroid, fensodium, ethyl fenthion, flucofuron, butylphosphide, phosphamidon, butylphosphide, furazolidone, pyrethroid, biguanide octyl salt, biguanide octyl acetate, sodium tetrathiocarbonate, benzyl ether, HCH, HEOD, heptachlor, phosmet, HHDN, hydrogen cyanide, quinoline, IPSP, chlorpyrifos, carbamate, isofenphos, isofenphos, transplanting agent, isoprothiolane, oxazolidinone, juvenile hormone I, juvenile hormone II, juvenile hormone III, chlorpyrifos, acetamiprid, lead arsenate, bromophenylphosphine, acetamiprid, thiamethoxam, m-isopropylphenyl methylcarbamate, magnesium phosphide, azide Phosphorus, methyl parathion, phosmet, mercurous chloride, methyl sulfoxide, phosmet, phosmet potassium salt, phosmet sodium salt, methyl sulfonyl fluoride, methoxypyridine, methoxypyrrolidine, methoxydichlorophenate, methyl isothiocyanate, methyl chloroform, dichloromethane, chlorpyrifos, fenpyroxene, naphthalene, NC-170, nicotine, nicotine sulfate, nitrazepam, protonicotinic acid, O-5-dichloro-4-iodophenyl O-ethyl ethyl thiophosphonate, O,O-diethyl O-4-methyl-2-oxo-2H-benzopyran-7-yl thiophosphonate, O,O-diethyl O-6-methyl-2-propylpyrimidin-4-yl thiophosphonate, O,O,O',O'-tetrapropyl dithiophosphate, oleic acid, p-dichlorobenzene, methyl parathion, pentachlorophenol, pentachlorophenyl laurate, pH 60-38, Fenthion, Parachlorfon, Phosphine, Methylphoxim, Methamphetamine, Polychlorinated dicyclopentadiene isomer, Potassium arsenite, Potassium thiocyanate, Precozid I, Precozid II, Precozid III, Aminopyrimidine, Procymidone, Mancozeb, Procymidone, Pyraclostrobin, Pyrethrum, Quassia extract, Quinalphos-methyl, Phosphamidon, Iodophos, Benzylfuran, Rotenone, Thiamethoxam, Rianodin, Sabadilla, Octylphos, Ketoconazole, SI-0009, Thiamethoxam, Sodium arsenite, Sodium cyanide, Sodium fluoride, Sodium hexafluorosilicate, Sodium pentachlorophenate, Sodium selenite, Sodium thiocyanate, Sulcofuron Sulcofuron-sodium, thiophanate-methyl, thiophanate-methyl, tar, thiamethoxam, TDE, butylpyrimidine phosphate, dithion, cyclopentenepyrethrin, tetrachloroethane, thiamethoxam, chlorpyrifos, chlorpyrifos oxalate, chlorpyrifos, chlorpyrifos mononitrate, chlorpyrifos sodium, tetrabromopyrethrin, transchlorfenapyr, azoxystrobin, trichlormetaphos-3, phosphonophosphorus, chlorpyrifos, tolprocarb, chlorpyrifos, tebufenozide, veratrine, veratrine, XMC, zetamethrin, zinc phosphide, chlorpyrifos, chlorfenapyr, tetrafluoroethylene, bis(tributyltin)oxide, bromoacetamideFerric phosphate, niclosamide-ethanolamine, tributyltin oxide, pyrmorpholine, spirochloride, 1,2-dibromo-3-chloropropane, 1,3-dichloropropene, 3,4-dichlorotetrahydrothiophene 1,1-dioxide, 3-(4-chlorophenyl)-5-methylrhodanine, 5-methyl-6-thio-1,3,5-thiadiazin-3-ylacetic acid, 6-isopentenylaminopurine, anisin, benclothiazide, cytokinin, DCIP, furfural, isamidophos, kinetin, *Lysimachia verrucae* composition, tetrachlorothiophene, xylenol, zeatin, potassium ethyl xanthate, aramidobenzene, aramidobenzene-S-methyl, *Reynoutria cuspidatum* Sachalinensis extract, α-chlorool, antagonist, barium carbonate, dimethomorph, bromadiolone, bromadiolone, bromadiolone methyl methacrylate, chlorpyrifos, cholecalciferol, chlorpyrifos, bromadiolone acetonide, bromadiolone acetonide, thiamethoxam, bromadiolone acetonide, calciferol, fluoroacetamide, fluoroacetamide, fluoroacetamide hydrochloride, bromadiolone acetonide, phosphatidylcholine, phosphatidylcholine, phosphatidylcholine, phosphatidylcholine, phosphatidylcholine, phosphatidylcholine, phosphatidylcholine, phosphatidylcholine, phosphatidylcholine, phosphatidylcholine, phosphatidylcholine, phosphatidylcholine, sodium fluoroacetate, thallium sulfate, phosphatidylcholine, 2-(2-butoxyethoxy)ethyl piperine, 5-(1,3-benzodioxane-5-yl)-3-hexylcyclohex-2-enone, farnesol with nerolidol, synergistic ether, MGK 264, synergistic ether, synergistic aldehyde, synergistic ester (propyl) isomer), S421, synergistic powder, sesasmolin, sulfoxide, anthraquinone, copper naphthenate, copper oxychloride, dicyclopentadiene, seren, zinc naphthenate, zinc thiram, imanin, ribavirin, chlorindolehydrazine, mercuric oxide, methyl thiophanate, azaconazole, bifenthrin, furazolidone, cymoxanil, difenoconazole, tebuconazole, flutriafol, cyproconazole, fluquinazole, flusilazole, fenpyroxenol, furazolidone, hexaconazole, imazalil, amide, tebuconazole, fenproxanil, cyproconazole, paclobutrazol, isoprothiolane, tebuconazole, prothioconazole, pyraclostrobin, imazalil, propiconazole, pyraclostrobin, tebuconazole, flufenoxuron, triadimefon, triadimefon, fluconazole, cymoxanil, pyrimidinol, chloropyrimidinol, ethirimol sulfonate (b (The remaining text appears to be a list of fungicides and their properties, which are not translated as they are not part of the main text.)Procymidone, vinclozoline, boscalid, carbendazim, methomyl, flutolanil, carbendazim, oxychloride, penthioopyrad, thifluzamide, doxycycline, biguanide octylamine, azoxystrobin, fenpyroxime, fenpyroxime, fenpyroxime, fluopyram, fluopyram, fenpyroxime, fenpyroxime, fenpyroxime, fenpyroxime, fenpyroxime, fenpyroxime, ferbamectin, mancozeb, mancozeb, propineb, mancozeb, captafol, captan, fluoroimide, captan, parathion, Bordeaux mixture, copper oxide Oxide, Mancozeb, Oxine-copper, Nitrothal-isopropyl, Iprobenphos, Phosdiphen, Tolclofos-methyl, Dimethoate, Benzothiamethoxam, Blasicidin-S, Chlorothalonil, Chlorothalonil, Cymoxanil, Diclocymet, Diclomezine, Dicloran, Dietofencarb, Dimethomorph, Flumorph, Dithianon, Ethaboxam, Etridiazole, Oxadiazon, Fenamidone, Fenoxanil Azoxystrobin (ferimzone), fluazinam, flumetylsulforim, fluopicolide, fluoxytioconazole, flusulfamide, fluazinam, cyclophosphamide, fosetylaluminium, hymexazol, propineb, cyazofamid, methasulfocarb, benomyl, pencycuron, phthalide, polyoxins, propamocarb, pyrofencarb, proquinazid, pyroquilon, pyriofenone, quinoxalic acid, pentachloronitrobenzene, thiamethoxam, imidacloprid, triazine, pyrazosulfuron, valerate, valacyclovirZoxamide, mandipropamid, fluopyramide, isopyrazam, sedaxane, benzovindiflupyr, fluopyroxypyrrolidone, 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3',4',5'-trifluoro-biphenyl-2-yl)-amide, isoflurane, isothiazamide, dipymetitrone, 6-ethyl-5,7-dioxo-pyrrolo[4,5][1,4]dithiainro[1,2-c]isothiazolyl-3-carboxylonitrile, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-indan-4-yl]pyridine Pyridine-3-carboxamide, 4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazin-3-carboxynitrile, (R)-3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazol-4-carboxamide, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-2,5-dimethyl-pyrazol-3-amine, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, fluazolidinone, methylphenidate, libenzan, dichlorophenoxythiazole, mandestrobin, 3-(4,4-difluoro-3,4- Dihydro-3,3-dimethylisoquinoline-1-yl)quinolone, 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinoline)oxy]phenyl]prop-2-ol, oxathiapiprolin, N-[6-[[[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]tert-butyl carbamate, piraziflumid, 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-formamidinium, N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidinium, [2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazole-1-yl]acetyl]-4-piperidinyl]thiazol-4-yl]-4,5-dihydroisoxazol-5-yl]-3-chloro-phenyl]methanesulfonate, N-[6-[[(Z)-[(1-methyltetrazole-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate butyl-3-yne 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)pyrazole-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one, 1-methyl-4-[3-methyl-2-[[2-methyl-4-(3,4,5-trimethylpyrazole-1-yl)phenoxy]methyl]phenyl]tetracycline] Azoxystrobin, aminopyrifen, pyraclostrobin, indoxazole, fluopyram, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamine, fluazinam, fenpicoxamid, methylpyridinium oxime, isobutylethoxyquinoline, iveflufenquin, quinoflavone, isoprophiazone, N-[2-[2,4-dichloro-phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazol-4-carboxamide, N-[2-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazol-4-carboxamide, fenpicoxamid Azoxystrobin, cyazofamid, 5-amino-1,3,4-thiadiazole-2-thiol zinc salt (2:1), fluopyram, flufenoxuron, fluoxastrobin, pyrimethanil, piperazine, 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, methyltetraproline, 2-(difluoromethyl) -N-((3R)-1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide, α-(1,1-dimethylethyl)-α-[4'-(trifluoromethoxy)[1,1'-diphenyl]-4-yl]-5-pyrimidinemethanol, flusaprolin, 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-thioalkyl-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile,4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thio-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, anti-dampness ester, eugenol, kasugamycin, thiamethoxam, thiamethoxam zinc, amitoline, iprodione, octochlor, N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidinium, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidinium, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-...] [Oxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidinium, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidinium, N'-[5-chloro-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidinium, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidinium (these compounds can be derived from WO4) Prepared by the method described in 2015 / 155075); N'-[5-bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N-methylformamidin (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-methylformamidin, N'-[4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-methoxy-2-methyl-phenyl]-N-isopropyl-N-methylformamidin (these compounds can be prepared by WO Prepared by the method described in 2018 / 228896); N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)oxetane-2-yl]phenyl]-N-methyl-formamidin, N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methyl-formamidin (these compounds can be prepared by WO Prepared by the method described in 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-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 derived from WO4) Prepared by the method described in 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-methylpyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline (these compounds can be prepared by WO Prepared by the method described in 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-isoquinoline)-7,8-dihydro-6H-cyclopentadien[e]benzimidazol (these compounds can be prepared by WO Prepared by the method described in 2016 / 156085); N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropaneformamide, N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide,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]propionamide, 4,4-dimethyl-2-[[4-[5-] (trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidine-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidine-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 derived from WO 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)prop-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-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)prop-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)prop-2-ol (this compound can be prepared by WO 2017 / 029179); Prepared by the method described in WO 2017 / 029179); 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazolium-4-carboxylonitrile (this compound can be prepared by the method described in WO 2016 / 156290); 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluorophenyl)-2-hydroxypropyl]imidazolium-4-carboxylonitrile (this compound can be prepared by the method described in WO 2016 / 156290); methyl 2-amino-6-methyl-pyridine-3-carboxylic acid (4-phenoxyphenyl) ester (this compound can be prepared by WO 2017 / 029179); Prepared by the method described in WO 2014 / 006945); 2,6-dimethyl-1H,5H-[1,4]dithiacino[2,3-c:5,6-c']dipyrrole-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]benzylthiocarboxamide; 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-enamine (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-formamidinium; N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidinium (this compound can be prepared by the method described in WO 2018 / 153707); Prepared by 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 by the method described in WO 2014 / 095675); (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl ketone, (3-methylisoxazol-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl ketone (these compounds can be prepared by WO 2016 / 202742); Prepared by the method described in WO 2017 / 220485); 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide (this compound can be prepared by the method described in WO 2018 / 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 WO 2017 / 220485); Prepared by 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]benzamide, N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, N-[N-methoxy-C-methyl-carbonimino]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide (these compounds can be prepared by the method described in WO 2018 / 202428).

[0042] 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 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-methyl-2-(2,4,6-trichloro-phenyl)ethyl]-1H-pyrazole-4-carboxamide (fluopyramidal hydroxylamine) to control or inhibit the effects of plant pathogenic bacteria.

[0043] Biological examples

[0044] Example 1 - Effects of fluopyram on leaf spot (bacterial leaf spot of tomato)

[0045] The experiment was conducted in the greenhouse of the Fruit Cultivation Department of the Federal University of Goiás. Temperature and humidity were controlled at this location. Tomato seedlings cv. Totalle with two true leaves were transplanted into 1L pots containing specialized growing medium. Two days after transplanting, the first application of the substances was performed. Bion (aranamic acid benzyl-S-methyl, 25g product / ha – 12.5g ai / ha), Miravis (fluopyram, 0.60kg product / ha – 120g ai / ha), Kocide (copper hydroxide, 1.50kg product / ha), and Kasumin (kasugamycin, 2L product / ha) were evaluated. The untreated control received only water. For application, the pots were placed on the ground and sprayed using a spraying device (with 6 nozzles spaced 0.5m apart) at a pressurized CO2 sprayer and a spray rate of 300L / ha.

[0046] Applications were made on days 1, 7, and 14. Inoculation with Xanthomonas perforatus isolate was performed on day 9 (between the second and third applications). All leaves of the plant were sprayed once with the pathogen suspension at a concentration of 10⁷ colony-forming units (cfu / mL). Assessments were performed three times post-inoculation at days 6, 13, and 18 (DAI), and the percentage of damaged leaves (area of ​​leaves with fungal plaque) was calculated.

[0047] Table 1. Damaged leaf area (%) observed in tomato plants inoculated with Xanthomonas perforatus at 6, 13 and 18 days (DAI) after inoculation.

[0048]

[0049] The data in Table 1 show that fluopyram provided good control of Xanthomonas perforatum up to 18 days after inoculation.

[0050] Example 2: Comparison of SDHI fungicide in the prevention of Xanthomonas oryzae (rice bacterial blight)

[0051] Three-week-old rice plants, cv. Balilla, were treated with the prepared test compound in a spray chamber. Two days after application, the rice plants were infected by cutting open the upper leaves and applying the bacterial suspension to the edges of the cut. After a 14-day incubation period at 23°C and 80% relative humidity, the disease level was visually assessed.

[0052] Table 2. Comparison of SDHI fungicides in the prevention of Xanthomonas rice / rice / fungi.

[0053]

[0054] The data in Table 2 show that fluopyram provided good control of Xanthomonas oryzae in the range of 20 to 60 mg ai / L, with little effect at 6 mg ai / L. Other SDHI fungicides tested did not provide control or inhibition of Xanthomonas oryzae.

[0055] Example 3: Effects of fluopyram on Xanthomonas aeruginosa on Zinnia elegans

[0056] Treat asexually propagated zinnia plants with fluopyram (targeting Xanthomonas or Pseudomonas) via foliar spraying. One to two days after treatment, mist the plants with a bacterial suspension (1 x 10⁸ CFU / mL, determined by spectrophotometry) and maintain at 100% relative humidity for 24 to 48 hours to promote infection. Then, keep the plants in a greenhouse or in a shady outdoor location and record the incidence and severity of disease, as well as plant health and fresh weight (if applicable).

[0057] Table 3. Effects of fluopyram on Xanthomonas aeruginosa on Zinnia elegans

[0058]

[0059] *Number of days after processing

[0060] The data in Table 3 show that fluopyram provides good control of Xanthomonas campestris.

[0061] Example 4. Effects of fluopyram on Larstonia spp. on Geranium.

[0062] Asexually propagated Geranium plants (Ralstonia) were treated by soaking in fluopyram. One to two days after treatment, the inoculum was treated by soil soaking. The plants were then kept in a greenhouse or in a shady outdoor location, and the incidence and severity of disease were recorded.

[0063] Table 4. Effects of fluopyram on Larstonia spp. on Geranium.

[0064]

[0065] It is an organic biological fungicide containing Bacillus subtilis as its active ingredient.

[0066] The data in Table 4 show that fluopyram provides control or inhibition against Larstonia spp.

Claims

1. A method for controlling or inhibiting plant pathogenic bacteria on beneficial plants, wherein the plant pathogenic bacteria is Xanthomonas campestris (…). Xanthomonas campestris Xanthomonas oryzae () Xanthomonas oryzae ) or Xanthomonas perforatum ( Xanthomonas perforans The method includes applying an effective amount of 3-(difluoromethyl)- N -Methoxy-1-methyl- N -[1-Methyl-2-(2,4,6-trichlorophenyl)ethyl]-1 H -Pyrazole-4-carboxamide is applied to the plant, plant parts or their location.

2. The method according to claim 1, comprising administering an effective amount of 3-(difluoromethyl)- N -Methoxy-1-methyl- N -[1-Methyl-2-(2,4,6-trichlorophenyl)ethyl]-1 H The composition of pyrazole-4-carboxamide is applied to the plant, plant part or site thereof.

3. The method according to claim 1 or claim 2, wherein, The useful plants mentioned are tomato, geranium, geranium, magnolia, rice, or zinnia.

4. The method according to any one of claims 1 to 2, wherein, 3-(difluoromethyl)- N -Methoxy-1-methyl- N -[1-Methyl-2-(2,4,6-trichlorophenyl)ethyl]-1 H 4-Pyrazole-4-carboxamide is applied to the plant, plant parts or its location at a rate of 20 g to 600 g per hectare.

5. The method according to any one of claims 1 to 2, wherein, 3-(difluoromethyl)- N -Methoxy-1-methyl- N -[1-Methyl-2-(2,4,6-trichlorophenyl)ethyl]-1 H 4-Pyrazole-4-carboxamide is applied to the plant, plant parts or its location at a rate of 40 g to 500 g per hectare. 6,3-(difluoromethyl)- N -Methoxy-1-methyl- N -[1-Methyl-2-(2,4,6-trichlorophenyl)ethyl]-1 H The use of pyrazole-4-carboxamide for controlling or inhibiting plant pathogenic bacteria on beneficial plants, wherein the plant pathogenic bacteria is Xanthomonas praecoxibacterium (…). Xanthomonas campestris Xanthomonas oryzae () Xanthomonas oryzae ) or Xanthomonas perforatum ( Xanthomonas perforans ).

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