Fungicidal compositions

Abstract

The present invention relates to novel fungicidal compositions, to their use in agriculture or horticulture for controlling diseases caused by phytopathogens, especially by phytopathogenic fungi, and to methods of controlling diseases on useful plants.

Description

Technical Field

[0001] This invention relates to novel antifungal compositions, their use in agriculture or horticulture for controlling diseases caused by plant pathogens (especially plant pathogenic fungi), and methods for controlling diseases on beneficial plants. Background Technology

[0002] Although many fungicidal compounds and compositions belonging to various chemical classes have been developed or are being developed for use as fungicides in beneficial plant crops, crop tolerance and activity against specific plant pathogens do not always meet the needs of agricultural practice in many respects. Therefore, there is a persistent need to discover new compounds and compositions with superior biological properties for the control or prevention of plant infection by plant pathogens. For example, compounds with greater biological activity, favorable activity spectra, increased safety, improved physicochemical properties, or increased biodegradability. Or, alternatively, compositions with broader activity spectra, improved crop tolerance, improved synergistic interactions or enhancing properties, or compositions exhibiting faster onset of action or longer residual activity, or compositions that reduce the number of applications and / or application rate required for effective control of plant pathogens, thereby enabling beneficial tolerance management practices, reducing environmental impact, and reducing operator exposure.

[0003] Some of these needs can be addressed by using compositions comprising mixtures of different fungicidal compounds with different modes of action (e.g., by combining fungicides with different activity spectra). Summary of the Invention

[0004] According to the present invention, an antifungal composition is provided, the antifungal composition comprising a mixture of components (A) and (B) as an active ingredient, wherein component (A) is a compound selected from:

[0005]

[0006]

[0007]

[0008]

[0009]

[0010] and

[0011] Component (B) is a cyanoacrylate compound.

[0012] In a preferred embodiment, component (A) is a compound selected from the following:

[0013]

[0014]

[0015] In a preferred embodiment, component (A) is N-[(1,2cis)-2-(2,4-dichlorophenyl)cyclobutyl]-2-(trifluoromethyl)pyridine-3-carboxamide (the ISO name of this compound is cyclobutrifluram).

[0016] The presence of one or more possible asymmetric carbon atoms in a compound means that the compound can exist in optical isomeric forms, i.e., enantiomers or diastereomers. As a result of restricted rotation around single bonds, transisomers may also exist. This invention includes all those possible isomeric forms of the compound (e.g., geometric isomers) and mixtures thereof. This invention includes all possible tautomeric forms of the compound, and also includes racemic compounds, i.e., mixtures of at least two enantiomers in a substantially 50:50 ratio.

[0017] In a preferred embodiment, component (A) comprises (1S,2S) and (1R,2R) enantiomers of the compound, and the ratio of the (1S,2S) enantiomer to the (1R,2R) enantiomer is greater than 4:1.

[0018] In a preferred embodiment, the ratio of the (1S,2S) enantiomer to the (1R,2R) enantiomer is greater than 1.5:1, greater than 2.5:1, greater than 4:1, greater than 9:1, greater than 20:1, or greater than 35:1.

[0019] In a preferred embodiment, the ratio of the (1S,2S) enantiomer to the (1R,2R) enantiomer is about 9:1.

[0020] In a preferred embodiment, component (A) is a pure (1S,2S) enantiomer.

[0021] If necessary, the final compound, which is pure in the enantiomeric sense, can be obtained from racemic material via standard physical separation techniques (e.g., reversed-phase chiral chromatography) or via stereoselective synthesis techniques (e.g., by using chiral starting materials).

[0022] The compounds of component (A) are commercially available and / or can be prepared using procedures known in the art and / or procedures reported in the literature (e.g., in WO 2013143811 or WO 2015003951, which are incorporated herein by reference in their entirety).

[0023] In each case, the compound according to the invention is in free form, oxidized form such as N-oxide, or salt form (e.g., in the form of an agronomically usable salt).

[0024] N-oxides are the oxidized forms of tertiary amines or nitrogen-containing heteroaromatic compounds. For example, they are described by A. Albini and S. Pietra in their 1991 book, "Heterocyclic N-oxides," published by CRC Press in Boca Raton.

[0025] In a preferred embodiment, component (B) is phenamacril, which has the IUPAC name (Z)-2-cyano-3-amino-3-phenylacrylate and has the following structure:

[0026]

[0027] Cyazofamid can be in free form, oxidized form such as N-oxide, or salt form. It is known and commercially available and / or can be prepared using procedures known in the art and / or procedures reported in the literature.

[0028] In a preferred embodiment, the weight ratio of component (A) to component (B) is from 40:1 to 1:150.

[0029] In a preferred embodiment, the weight ratio of component (A) to component (B) is from 20:1 to 1:150.

[0030] In a preferred embodiment, the weight ratio of component (A) to component (B) is from 20:1 to 1:100.

[0031] In a preferred embodiment, the weight ratio of component (A) to component (B) is from 20:1 to 1:50.

[0032] In a preferred embodiment, the weight ratio of component (A) to component (B) is from 1:50 to 1:100.

[0033] In a preferred embodiment, component (A) is N-[(1,2cis)-2-(2,4-dichlorophenyl)cyclobutyl]-2-(trifluoromethyl)pyridine-3-carboxamide or its salt, enantiomer or N-oxide, and component (B) is cyazofamid in free form, oxidized form such as N-oxide or salt form, wherein the weight ratio of component (A) to component (B) is from 20:1 to 1:50 or 1:50 to 1:100.

[0034] In addition, according to the present invention, a method for controlling or preventing plant pathogenic diseases, especially plant pathogenic fungi, on useful plants or their propagation material is provided, the method comprising applying a fungicidal composition according to the present invention to such useful plants, their sites or their propagation material.

[0035] The benefits provided by certain fungicidal mixture compositions according to the invention may also include, in particular, favorable levels of bioactivity for protecting plants against fungal diseases or superior properties for use as an agrochemical active ingredient (e.g., greater bioactivity, favorable activity spectrum, increased safety, improved physicochemical properties, or increased biodegradability).

[0036] As used herein, the term "fungicide" refers to a compound that controls, alters, or prevents the growth of fungi. The term "effective fungicide amount" refers to the amount of one or a combination of such compounds that can affect fungal growth. Controlling or altering effects include all deviations from natural development, such as killing, inhibiting, etc., and prevention includes the formation of barriers or other defenses within or on the plant to prevent fungal infection.

[0037] The term "plant" refers to all the tangible parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, culms, leaves, and fruits.

[0038] The term "plant propagation material" refers to all reproductive parts of a plant, such as seeds or vegetative parts like cuttings and tubers. It includes seeds in the strict sense, as well as roots, fruits, tubers, bulbs, rhizomes, and other parts of the plant.

[0039] 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.

[0040] Throughout this document, the term "composition" refers to different mixtures or combinations of components (A) and (B) (including the embodiments defined above), for example, in a single "ready-to-use with water" form, as a combined spray mixture (consisting of individual formulations of these single active ingredient components) (e.g., a "tank mix"), and as a combination of these single active ingredients when applied in a sequential manner (i.e., one after the other after a suitable short period, such as hours or days). For the purposes of this invention, the order in which components (A) and (B) are applied is not critical.

[0041] The compositions according to the present invention are effective against harmful microorganisms (such as microorganisms) that cause plant pathogenic diseases, especially against plant pathogenic fungi and bacteria.

[0042] The compositions of the present invention can be used to control plant diseases caused by a broad spectrum of fungal plant pathogens belonging to the classes Basidiomycete, Ascomycete, Oomycete and / or Deuteromycete, Blastodactylomycete, Chrytidiomycete, Glomeromycete and / or Mucoromycete.

[0043] This composition effectively controls a broad spectrum of plant diseases, such as leaf pathogens in ornamental plants, turf, vegetables, fields, cereals, and fruit crops.

[0044] These pathogens may include:

[0045] Oomycetes include Phytophthora diseases, such as those caused by *Phytophthora capsici*, *Phytophthora infestans*, *Phytophthora sojae*, *Phytophthora fragariae*, *Phytophthora nicotianae*, *Phytophthora cinnamomi*, *Phytophthora citricola*, *Phytophthora citrophthora*, and *Phytophthora erythroseptica*; and Pythium diseases, such as those caused by *Pythium aphanidermatum*, *Pythium arrhenomanes*, *Pythium graminicola*, *Pythium irregulare*, and *Pythium tertrum*. Diseases caused by *Peronospora destructor*, *Peronospora parasitica*, *Plasmopara viticola*, *Plasmopara halstedii*, *Pseudoperonospora cubensis*, *Albugo candida*, *Sclerophthoramacrospora*, and *Bremia lactucae*; and others, such as *Aphanomyces cochlioides*, *Labyrinthula zosterae*, *Peronosclerospora sorghi*, and *Sclerospora graminicola*.

[0046] Ascomycetes, including diseases such as spot, blight, wilt, or downy mildew and / or rot, such as those caused by: Pleosporales, including Stemphylium solani (garlic white spot fungus), Stagonospora tainanensis (Tainan daffodil), Cyclophorus oleiferus (olive bark fungus), Setosphaeria turcica (corn large leaf spot fungus), Pyrenochaeta lycoperisici (tomato bark fungus), Pleospora herbarum (leaf lichen fungus), Phona destructiva (stem rot fungus), Phaeosphaeria herpotrichoides (wheat leaf dark spot fungus), Phaeococcus gaeumannii (brown cryptococcus fungus), Ophiosphaerella graminicola (grass spore fungus), Ophiobolus graminis (wheat take-all fungus), Leptosphaeria maculans (cruciferous small spore fungus), and Hendersonia (soft rot fungus). *Creberrima*, *Helminthosporium triticirepentis*, *Setosphaeria turcica*, *Drechsleraglycines*, *Didymella bryoniae*, *Cycloconium oleagineum*, *Corynespora cassiicola*, *Cochliobolus sativus*, *Bipolaris cactivora*, *Venturiainaequalis*, *Pyrenophora teres*, *Pyrenophora tritici-repentis*, *Alternaria alternata*, *Alternaria brassicicola*, *Alternaria solanacea* *Septoria solani* and *Alternaria tomatophila*; Capnodiales such as *Septoria tritici*, *Septoria nodorum*, and *Septoria spp.*The fungi causing the following diseases are listed: *Cercospora aracidola*, *Cercospora sojina*, *Cercospora zeae-maydis*, *Cercosporella capsellae*, *Cercosporella herpotrichoides*, *Cladosporium carpophilum*, *Cladosporium effusum*, *Passalora fulva*, *Cladosporium oxysporum*, *Dothistroma septosporum*, *Isariopsis clavispora*, *Mycosphaerella graminicola*, *Mycovellosiella koepkeii*, and *Phaeoisariopsis*. * *Pseudocercospora vitis*, *Pseudocercospora*, *Pseudocercospora*, *Pseudocercospora*, *Pseudocercospora*, *Pseudocercospora*, *Pseudocercospora*, *Pyricularia ... *Phomopsis viticola*, *Sirococcus clavigignenti-juglandacearum*, *Tubakia dryina*, and species of the genus *Dicarpella*.*Valsa ceratosperma*, a fungus causing apple tree rot; and others such as *Actinothyrium graminis*, *Ascochyta pisi*, *Aspergillus flavus*, *Aspergillus fumigatus*, *Aspergillus nidulans*, *Asperisporium caricae*, *Blumeriella jaapii*, *Coccidioides spp.*, *Capnodium ramosum*, *Cephaloascus spp.*, *Cephalosporium gramineum*, *Ceratocystis paradoxa*, and *Chaetomium* species. spp.), Hymenoscyphus pseudoalbidus, Coccidioides spp., Cylindrosporium padi, Diplocarpon malae, Drepanopeziza campestris, Elsinoe ampelina, Epicoccum nigrum, Epidermophyton spp., Eutypa lata, Geotrichum candidum, Gibellina cerealis, Gloeocercospora sorghi, Gloeodes pomigena, Gloeosporium perennans; Gloeotinia temulenta, Griphospaeria Corticola, Kabatiella lini, Leptographium microsporum, Leptosphaerulinia crassiasca, Lophodermium seditiosum, Marssonina* *Graminicola*, *Microdochium nivale*, *Monilinia fructicola*, *Monographella albescens*, *Monosporascus cannonballus*, *Naemacyclus* spp., *Ophiostoma novo-ulmi*, *Paracoccidioides brasiliensis*, *Penicillium expansum*, *Pestalotia rhododendri*, *Petriellidium* spp., *Pezicula* spp., *Phialophora gregata*, *Phyllachora pomigena*, *Phymatotrichumomnivora*, *Physalospora* abdita), tobacco spore shell (Plectosporium tabacum), potato skin spot fungus (Polyscytalum pustulans), alfalfa pseudodisc (Pseudopeziza medicaginis), brassicae sclerotiorum (Pyrenopeziza brassicae), sorghum spore spore (Ramulis porasorghi), Douglas fir leaf spot fungus (Rhabdocline pseudotsugae), barley cloud spot fungus (Rhynchosporium secalis), rice broom broom (Sacrocladium oryzae), species of the genus Scedosporium spp., pome spore spore (Schizothyrium pomi), sclerotinia sclerotiorum, small sclerotinia (Sclerotinia minor); species of the genus Sclerotium spp.), Typhulaishikariensis, Seimatosporium mariae, Lepteutypacupressi, Septocyta ruborum, Sphaceloma perseae, SporonemaPowdery mildew, including fungi such as *Stigmina palmivora*, *Tapesia yallundae*, *Taphrina bullata*, *Thielviopsis basicola*, *Trichoseptoria fructigena*, and *Zygophiala jamaicensis*; and powdery mildew, such as those from the order Erysiphales, including *Blumeria graminis*, *Erysiphe polygoni*, *Uncinulanecator*, *Sphaerotheca fuligena*, *Podosphaeraleucotricha*, *Podospaera macularis*, *Golovinomyces cichoracearum*, and *Leveillula*. Those caused by *Taurica*, *Microsphaeradiffusa*, *Oidiopsis gossypii*, *Phyllactinia guttata*, and *Oidium arachidis*; molds, such as those caused by *Botryosphaeriales* like *Dothiorella aromatica*, *Diplodiaseriata*, *Guignardia bidwellii*, *Botrytis cinerea*, *Botryotinia allii*, *Botryotinia fabae*, *Fusicoccum amygdali*, *Lasiodiplodia theobromae*, *Macrophoma theicola*, *Phyllosticta*, and others. Anthracnose caused by *Colletotrichum gloeosporioides*, *Colletotrichum lagenarium*, and *Colletotrichum cucurbitacearum*.Those caused by *Gastrodia elata*, *Glomerella cingulata*, and *Colletotrichum graminicola*; and wilt or blight, such as those caused by Hypocreales such as *Acremonium strictum*, *Claviceps purpurea*, *Fusarium culmorum*, *Fusarium graminearum*, *Fusarium proliferatum*, *Fusarium virguliforme* (soybean sudden death syndrome fungus), *Fusarium oxysporum*, *Fusarium subglutinans*, *Fusarium oxysporum f.sp. cubense*, *Gerlachia nivale*, *Gibberella fujikuroi*, and *Gibberella zearalensis*. Those caused by *Zeae*, *Gliocladium* spp., *Myrothecium verrucaria*, *Nectria ramulariae*, *Trichoderma viride*, *Trichothecium roseum*, and *Verticillium theobromae*;

[0047] Basidiomycetes include diseases such as smut caused by Ustilaginales (e.g., *Ustilaginoidea virens*, *Ustilago nuda*, *Ustilagotritici*, *Ustilago zeae*) and rust diseases caused by Pucciniales (e.g., *Cerotelium fici*, *Chrysomyxa arctostaphyli*, *Coleosporium ipomoeae*, *Hemileia vastatrix*, *Puccinia arachidis*, *Puccinia cacabata*, *Puccinia graminis*, *Puccinia recondita*, *Puccinia sorghi*, and *Puccinia sorghi*). Those rusted by *Puccinia striiformis* f.sp. Hordei, *Puccinia striiformis* f.sp. Secalis, and *Pucciniastrum coryli*; or those from the order Uredinales such as *Cronartium ribicola*, *Gymnosporangium juniperi-viginianae*, *Melampsora medusae*, *Phakopsora pachyrhizi*, *Phragmidium mucronatum*, *Physopella ampelosidis*, *Tranzschelia discolor*, and *Uromyces*. Those caused by *Viciae-fabae*; and other rots and diseases, such as those caused by species of the genus *Cryptococcus*, *Exobasidium vexans*, *Marasmiellus inoderm*, and *Mycena*.The fungi causing the following diseases are: *Sphacelotheca reiliana*, *Typhula ishikariensis*, *Urocystis agropyri*, *Itersonilia perplexans*, *Corticium invisum*, *Laetisaria fuciformis*, *Waitea circinata*, *Rhizoctonia solani*, *Thanetephorus cucurmeris*, *Entyloma dahliae*, *Entylomella microspora*, *Neovossia moliniae*, and *Tilletia caries*.

[0048] Bulbophyllum class, such as Physoderma maydis;

[0049] Mucormycetes, such as *Choanephora cucurbitarum*; species of the genus *Mucor* (*Mucor spp.*); *Rhizopus arrhizus*;

[0050] Together with diseases caused by other species and genera closely related to those listed above.

[0051] In addition to their antifungal activity, these compositions may also have activity against bacteria such as Erwinia amylovora, Erwinia caratovora, Xanthomonas campestris, Pseudomonas syringae, Strptomyces scabies and other related species, along with certain protozoa.

[0052] The compositions according to the invention are particularly effective against plant pathogenic fungi belonging to the following classes: Ascomycetes (e.g., *Aureobasidium*, *Cyclocarya*, *Erythrophagus*, *Cyclocarya*, *Cyclocarya*, *Uncaria*); Basidiomycetes (e.g., *Hemileia*, *Rhizoctonia*, *Laminaria*, *Pseudomonas*, *Ustilago*, *Ustilago*); Deuteromycetes (also known as Deuteromycetes, e.g., *Botrytis*, *Helicobacter*, *Rhizoctonia*, *Fusarium*, *Syndrome*, *Cercospora*, *Alternaria*, *Pyrophora*, and *Pseudomonas*); Oomycetes (e.g., *Phytophthora*, *Peronospora*, *Pseudomonas*, *Eucorus*, *Plasmodium*, *Pythium*, *Pseudomonas*, *Pseudomonas*, *Pseudomonas*, *Pseudomonas*, *Pseudomonas*, *Pseudomonas*, *Pseudomonas*, *Pseudomonas*).

[0053] In preferred embodiments, the compositions according to the invention are particularly effective against wheat scab caused by Fusarium head blight and rice bakanae caused by Fusarium moniliforme or Fusarium fuciformis.

[0054] The compositions according to the invention can be used in useful plant crops including perennial and annual crops, such as berry plants, such as blackberries, blueberries, cranberries, raspberries, and strawberries; cereals, such as barley, corn, millet, oats, rice, rye, sorghum, triticale, and wheat; fiber plants, such as cotton, flax, hemp, jute, and sisal; field crops, such as sugar beets and forage beets, coffee beans, hops, mustard, canola, poppies, sugarcane, sunflowers, tea, and tobacco; fruit trees, such as apples, apricots, avocados, bananas, cherries, citrus fruits, nectarines, peaches, pears, and plums; and grasses, such as Bermuda grass, bluegrass, benjamin grass, centipede grass, yew grass, and ryegrass. St. Augustine grass and zoysia grass; herbs such as basil, borage, chives, coriander, lavender, angelica, mint, oregano, parsley, rosemary, sage, and thyme; legumes such as kidney beans, lentils, peas, and soybeans; nuts such as almonds, cashews, peanuts, hazelnuts, peanuts, pecans, pistachios, and walnuts; palm trees such as oil palms; ornamental plants such as flowers, shrubs, and trees; other trees such as cacao, coconut, olive, and rubber trees; vegetables such as asparagus, eggplant, broccoli, cabbage, carrots, cucumbers, garlic, lettuce, zucchini, melons, okra, onions, peppers, potatoes, squash, rhubarb, spinach, and tomatoes; and grapevines such as grapes.

[0055] Crops should be understood as those that exist naturally, are obtained through conventional breeding methods, or are obtained through genetic engineering. These include crops with so-called output traits (such as improved storage stability, higher nutritional value, and improved flavor).

[0056] Crops should be understood to include those crops that have been conferred tolerance to herbicides (like bromoxynil) or multiple classes of herbicides (such as ALS-, EPSPS-, GS-, HPPD-, and PPO- inhibitors). Examples of crops that have been conferred tolerance to imidazolinones (e.g., imazamox) through conventional breeding methods are... Summer Canola. Examples of crops conferred herbicide tolerance through genetic engineering include, for example, glyphosate and glufosinate-resistant maize varieties, which are marketed under trademarks... Herculex and It is available for commercial purchase.

[0057] Crops should also be understood as those that are naturally or have been conferred resistance to harmful insects. This includes plants that, for example, are capable of synthesizing one or more selectively acting toxins through the use of recombinant DNA technology, such toxins as those known from toxin-producing bacteria. Examples of toxins that can be expressed include delta-endotoxins, vegetative insecticidal proteins (Vip), insecticidal proteins of nematode-parasitic bacteria, and toxins produced by scorpions, arachnids, wasps, and fungi.

[0058] An example of a crop that has been modified to express Bacillus thuringiensis toxin is Bt maize. (Syngenta Seeds). Examples of crops containing more than one gene encoding insecticidal resistance and thus expressing more than one toxin are: (Syngenta Seeds). Crops or their seed material can also be resistant to multiple types of pests (so-called superimposed transgenic events when produced through genetic modification). For example, plants can express insecticidal proteins while being resistant to herbicides, such as Herculex. (Dow AgroSciences, Pioneer Hi-Bred International)

[0059] In a preferred embodiment, the composition according to the invention is used to control or prevent plant pathogenic diseases in cereals, preferably wheat or rice.

[0060] The compositions of the present invention, including all the embodiments and preferred examples disclosed above, can be mixed with one or more other pest control agents, including additional fungicides, insecticides, nematicides, bactericides, acaricides, growth regulators, chemical sterilizers, chemical pheromones, insect repellents, attractants, pheromones, feeding stimulants, or other bioactive compounds to form multi-component pest control agents that provide broader-spectrum agricultural protection.

[0061] Examples of such agricultural protectants that can be used to formulate the compositions of the present invention include:

[0062] Choose from the following groups of substances: petroleum, 1,1-bis(4-chloro-phenyl)-2-ethoxyethanol, 2,4-dichlorophenyl benzenesulfonic acid, 2-fluoro-N-methyl-N-1-naphthylacetamide, 4-chlorophenylphenyl sulfone, acetamiprid, thiamethoxam, cypermethrin, phosmet, methamidophos, methamidophos oxalate, amitraz, dicofol, arsenic trioxide, azobenzene, azophos, benomyl, benzyl benzoate, benzyl benzoate. Bifenthion, bromocypermethrin, bromo-cyclohexane, bromothion, bromodiphenyl ether, thiamethoxam, methyl ethyl ketone, methyl ethyl ketone sulfonate, butylpyridaben, calcium polysulfide, camphene, chlorfenapyr, trichlorfon, acaricide, dicofol, amitraz, amitraz hydrochloride, dicofol, dicofol, difenoconazole, ethyl dicofol, amitraz, dicofol, propyl ester, chlorfenapyr, fenpropathrin I, fenpropathrin II, fenpropathrin, cloxacillin, phosmet, cloxacillin Phosphate, thiophanate-methyl, phosmet, DCPM, DDT, phosmet-O, ​​phosmet-S, phosmet-methyl, phosmet-O, ​​phosmet-O-methyl, phosmet-S, phosmet-S-methyl, phosmet, chlorpyrifos, dichlorvos, dichlorvos, chlorpyrifos, methylflufenoxam, dinex, dinex-diclexine, difenoconazole-4, difenoconazole-6, chlorpyrifos, nitrate Amyl ester, nitrocellulose ester acaricide, nitrobutyl ester, dichlorvos, sulfadiazine, disulfiram, DNOC, dofenapyn, dofenapyn, phosmet, phenoxyacetic acid, fentrifanil, fenthion, fenthion, fenpyrad, fenpyroxen, fentrifanil, fenthion ... 1137, chlorfenapyr, chlorfenapyr hydrochloride, formocarb, γ-HCH, chlorfenapyr, benzoyl permethrin, hexadecyl cyclopropanecarboxylate, methamidophos, jasmine ester I, jasmine ester II, iodophos, lindane, propiconazole, pymetrozine, dithiamethoxam, methamidophos, chlorfenapyr, methyl bromide, methamidophos, milbemime, propanil, phorate, malathion, moxifloxacin, dibromophos, 4-chloro-2-(2-chloro-2-methyl-propyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazin-3-one, flufenoxuron, nicotinamide Cypermethrin, cypermethrin 1:1 zinc chloride complex, omethoate, isosulfanilamide, phosmet, pp'-DDT, parathion, permethrin, fenthion, phosmet, phosphamidon, polychloroterpenes, polynactins, prochloraz, carbendazim, propoxur, ethiophanate-methyl, phosmet, pyrethrin I, pyrethrin II, pyrethrin, pyridaben, pyrimethanil, quinalphos, quintiofos, R-1492, glyphosate,Rotenone, octamethrin, chlorpyrifos, silachlor, thiophanate-methyl, SSI-121, sulphurin, fipronil, thiophanate-methyl, sulfur, flufenoxam, t-flufenoxam, tebufenozide, terbufos, tetrachlorfon, thiafenoxam, chlorfenapyr, methyl methamidophos, chlorfenapyr, thiamethoxam, fenpyroxine, bethoxazin, copper dioctanoate, copper sulfate, cyprodinium, dichloronaphthoquinone, dichlorophenol, cymoxanil, triphenyltin, quicklime, sodium mancozeb, cymoxanil, quinoline, simazine Zinc, 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, doxorubicin, sodium dichloroisocyanurate, formaldehyde, mercurochrome, kasugamycin, kasugamycin hydrochloride hydrate, bis(dimethyldithiocarbamate)nickel, trichloromethylpyridine, octothiazoline, oxadiazine, 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, *Aphidoletesaphidimyza*, alfalfa silver-striped noctuid moth NPV, *Bacillus sphaericus Neide*, *Beauveria brongniartii*, common lacewing (*Chrysoperla carnea*), *Cryptolaemus montrouzieri*, codling moth GV, *Dacnusa sibirica*, pea leafminer fly pygmy wasp (*Diglyphus isaea*), *Encarsia formosa*, *Eretmocerus eremicus*, *Heterorhabditis* bacteriophora, and the large heterocerca nematode (H. megidis), the spotted ladybug (Hippodamia convergens), the citrus scale parasitic wasp (Leptomastix dactylopii), the mirid bug (Macrolophus caliginosus), the cabbage looper NPV,The following species were included in the list of nematodes: *Metaphycus helvolus*, *Metarhizium anisopliae var. acridum*, *Metarhizium anisopliae var. anisopliae*, *Neodiprion sertifer* NPV and *N. lecontei* NPV, *Orius spp.*, *Paecilomyces fumosoroseus*, *Phytoseiulus persimilis*, *Steinernema bibionis*, *Steinernema carpocapsae*, *Steinernema glaseri*, *Steinernema riobrave*, and *Steinernema reesei*. riobravis), Steinernema scapterisci, species of the genus Steinernema spp., species of the genus 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)-Dodeca-7-en-1-yl acetate, (Z)-Hexadec-11-enal, (Z)-Hexadec-11-en-1-yl acetate, (Z)-Hexadec-13-en-11-ynyl acetate, (Z)-Eicosyl-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-Methylnon-5-ol and 4-Methylnon-5-one, α-polystyrin, western pine bark beetle pheromone, dodecadienol (codlelure), codlemone, cuelure, nonadecane oxide, dodecadien-8-yl acetate, dodecadien-9-yl acetate, dodecadien-8-yl acetate 10-Dien-1-yl ester, Domi attractant, ethyl 4-methyloctanoate, eugenol, frontalin (for southern pine bark beetle), grandlure (forelegene mixture), hexalure (forelegene mixture I, II, III, IV), ipsdienol (for tooth beetle), ipsenol (forelegene), japonilure (for scarab beetle), lineatin (forelegene), noctuid moth attractant, and *Hemibarbus erythropterus* (forelegene beetle). Sex pheromone (looplure), medlure, (3E,5Z)-tetradec-3,5-dienoic acid, methyleugenol, muscalure, octadec-2,13-dien-1-yl acetate, octadec-3,13-dien-1-yl acetate, orfralure, oryctalure (coconut beetle aggregation pheromone), ostramone, siglure, sordidin (in), 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 Carbate, dimethyl phthalate, ethylhexanediol, hexamide, methoquin-butyl, methylneodecanamide, 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 phosphate 2-ethylsulfinyl ethyl ester methyl ester, dimethylcarbamate 2-(1,3-dithiopentane-2-yl)phenyl ester, thiocyanate 2-(2-butoxyethoxy)ethyl ester, methylcarbamate 2-(4,5-dimethyl-1,3-dioxolane-2-yl)phenyl ester, 2-(4-chloro-3,5-dimethylmethyloxy)ethanol, 2-chlorovinyl phosphate diethyl ester, 2-imidazolinone, 2-isovalerylindan-1,3-dione, methylcarbamate 2 2-Methyl(prop-2-ynyl)aminophenyl ester, 2-cyanothioethyl laurate, 3-bromo-1-chloroprop-1-ene, 3-methyl-1-phenylpyrazole-5-yl dimethylcarbamate, 4-methyl(prop-2-ynyl)amino-3,5-dimethylcarbamate, 5,5-dimethyl-3-oxocyclohexyl-1-enyl dimethylcarbamate, acethromycin, acrylonitrile, aldrin, aprotinin, chlorpyrifos, α-decanoic acid, aluminum phosphide, carbendazim, neonicotinoids, ethyl chlorpyrifos (athidathion), methylpyridinium, Bacillus thuringiensis δ-endotoxin, barium hexafluorosilicate, barium polysulfide, pyrethroid, Bayer 22 / 190, Bayer 22408, β-cypermethrin, β-cypermethrin, bioethanomethrin, permethrin, bis(2-chloroethyl) ether, borax, bromophenylenephos, bromo-DDT, chlorpyrifos, pyrimethanil, butathiofos, butyl phosphate, calcium arsenate, cyanide Calcium, carbon disulfide, carbon tetrachloride, batan hydrochloride, cevadine, borneol, chlordane, decachlorophenone, chloroform, chloropicrin, chlorpyrifos oxime, chlorprazophos, cis-resmethrin, d-benzylfuran, clocythrin, copper acetylacetonate, copper arsenate, copper oleate, coumithoate, cryolite, CS 708, Benzoate, Phytazonium, Cypermethrin, Cypermethrin, d-methoxyfenozide, DAEP, Dazomet, Decarbofuran, Diamidafos, Isochlor, Dicresyl, Cypermethrin, Dildrin, Diethyl phosphate 5-methylpyrazol-3-yl ester, Dior, Tetrafluoromethrin, Dimethoate, Permethrin, Methyl chlorpyrifos, Difenoconazole, Pronitrophenol, Pendimethalin, Diphenoxyphenoxyphene, Fipronil, Phosphafen, Thiamethoxam, DSP, Edermalin, EI 1642, EMPC, EPBP, etaphos, ethylcarbide, ethyl formate, dibromoethane, dichloroethane, ethylene oxide, EXD, phosmet, ethylcarbide, fenitrothion, fenoxacrim, pyrethroid, fensodium, ethyl fensodium, flucofuronButylbenzyl phosphonate, phosphonopropamide, butylphosphonate, furazolidone, pyrethrum, biguanide octyl salt, biguanide octyl acetate, sodium tetrathiocarbonate, benzyl ether, HCH, HEOD, heptachlor, chlorpyrifos, HHDN, hydrogen cyanide, quinoline carbide, IPSP, chlorpyrifos, carbamate, isofenphos, isofenphos, transplanting agent, isoprothiolane, oxazolium, juvenile hormone I, juvenile hormone II, juvenile hormone III, chlorpyrifos, acetamiprid, lead arsenate, bromobenzyl phosphonate, acetamiprid, thiamethoxam, m-isopropylphenyl methylcarbamate, magnesium phosphide, azidophos, methyl pymetrozine, pymetrozine, mercurous chloride, methyl sulfoxide, pymetrozine potassium salt, pymetrozine sodium salt, methanesulfonyl fluoride, butylbenzyl phosphonate Enamiphos, methoxypurine, methoxydiphenyl ether, methoxydichlorophenate, methyl isothiocyanate, methyl chloroform, dichloromethane, chlorpyrifos, fenvalerate, naphthalene, NC-170, nicotine, nicotine sulfate, nitrazepam, protonicotinic acid, thiophosphonic acid O-5-dichloro-4-iodophenyl ester O-ethyl ethyl ester, thiophosphonic acid O,O-diethyl ester O-4-methyl-2-oxo-2H-benzopyran-7-yl ester, thiophosphonic acid O,O-diethyl ester O-6-methyl-2-propylpyrimidin-4-yl ester, dithiophosphate O,O,O',O'-tetrapropyl ester, oleic acid, p-dichlorobenzene, methyl parathion, pentachlorophenol, pentachlorophenyl laurate, pH 60-38, Fenthion, Parachlorfenapyr, Phosphine, Methyl phoxim, Methamphetamine, Polychlorinated dicyclopentadiene isomer, Potassium arsenite, Potassium thiocyanate, Precozid I, Precozid II, Precozid III, Aminopyrimidine phosphate, Procymidone, Mancozeb, Procymidone, Pyraclostrobin, Pyrethrum, Quassia extract, Quinalphos-methyl, Phosphine, Iodophos, Benzylfuran, Rotenone, Thiamethoxam, Rianodine, Sabadilla, Octylphos, Ketoconazole, SI-0009, Thiamethoxam, Sodium arsenite, Sodium cyanide, Sodium fluoride, Sodium hexafluorosilicate, Sodium pentachlorophenate, Sodium selenate, Sodium thiocyanate, Sulcofuron, Sulcofuron-sodium, Thionyl fluoride, Thiophanate, Tar Thiamethoxam, TDE, Butyrimidine, Dithion, Cypermethrin, Tetrachloroethane, Thiamethoxam, Cypermethrin Oxalate, Cypermethrin, Cypermethrin Sodium, Tetrabromopyrethrin, Transchlorpyrifos, Azoxystrobin, Trichlormetaphos-3, Phosphine, Mixed carbendazim, Tolprocarb, Chlorpyrifos, Acetaminophen, Veratrum nigrum, Veratrum alkaloid, XMC, Zetamethrin, Zinc phosphide, Azoxystrobin, Cypermethrin, Bis(tributyltin)oxide, Bromoacetamide, Ferric phosphate, Niclosamide-ethanolamine, Tributyltin oxide, Pyrmorpholine, Serochloride, 1,2-Dibromo-3-chloropropane, 1,3-Dichloropropene, 3,4-Dichlorotetrahydrothiophene 1,1-dioxide3-(4-Chlorophenyl)-5-methylrhodanine, 5-methyl-6-thio-1,3,5-thiadiazin-3-ylacetic acid, 6-isopentenylaminopurine, anisiflupurin, benclothiazide, cytokinin, DCIP, furfural, isamidophos, kinetin, *Lysimachia verrucae* composition, tetrachlorothiophene, xylenol, zeatin, potassium ethyl xanthate, aramidobenzene, aramidobenzene-S-methyl, *Reynoutria sachalinensi* s) extract, α-chlorool, antor, barium carbonate, dimethomorph, bromadiolone, bromadiolone, bromadiolone acetonide, chlorpyrifos, cholecalciferol, chlorpyrifos, bromadiolone acetonide, bromadiolone acetonide, thiamethoxam, bromadiolone acetonide, calciferol, fluoroacetamide, fluoroacetamide, fluoroacetamide hydrochloride, bromadiolone acetonide, phosmet, phosmet, bromadiolone acetonide, bromadiolone acetonide, hyoscyamine, safflower glycoside, sodium fluoroacetate, thallium sulfate, bromadiolone, 2-(2-butoxyethoxy)ethyl ester of piperic acid, 5-(1,3-benzodiazepine-5-yl)-3-hexylcyclohex-2-enone, farnesol and nerolidol, synergistic alkyne ether, MGK 264. Synergistic ethers, synergistic aldehydes, synergistic esters (propylisome), S421, synergistic powder, sesasmolin, sulfoxide, anthraquinone, copper naphthenate, copper oxychloride, dicyclopentadiene, serene, zinc naphthenate, zinc fumarate, imanin, ribavirin, chloroinconazide, mercuric oxide, methyl thiophanate, azaconazole, bifenthrin, furazolidone, cyclozole Alcohol, difenoconazole, tebuconazole, fluconazole, cyproconazole, fluquinazole, flusilazole, fenbendazole, furazolidone, hexaconazole, imazalil, imidacloprid, tebuconazole, cyproconazole, paclobutrazol, isoprothiolane, tebuconazole, prothioconazole, pyrifenoxam, imazalil, propiconazole, simeconazole, tebuconazole, flufenoxam, triadimefon, triadimefon, fluconazole, simeconazole Pyrimidinol, Chlorpheniramineol, Flupheniramineol, Bupirimate, Dimethirimol, Ethirimol, Dodecylmorpholine, Fenpropidin, Butylmorpholine, Spirocyclohexane, Tridemorpholine, Azoxystrobin, Azoxystrobin, Pyrimethanil, Seed dressing, Fludioxonil, Benalaxyl, Furalaxyl, Metalaxyl, R Metalaxyl, Furazolidone, Oxadixyl, Carbendazim, Debacarb, Wheat bran, Thibendazole, Chlozolinate, Dichlozoline, Myclozoline, ProcymidoneVinclozoline, boscalid, carbendazim, methomyl, flutolanil, carbendazim, oxychloride, penthioopyrad, thifluzamide, doxycycline, biguanide octylamine, azoxystroburin, fenfluroxystroburin, fluopyram, fluopyram, azoxystroburin, fenfluroxystroburin, fenfluroxystroburin, fenfluroxystroburin, fenfluroxystroburin, fenfluroxystroburin, fenfluroxystroburin, fenfluroxystroburin, fenfluroxystroburin, fenfluroxystroburin, fenfluroxystroburin, fenfluroxystroburin, fenfluroxystroburin, fenfluroxystroburin, fenfluroxystroburin, fenfluroxystroburin, fenfluroxystroburin, fenfluroxystroburin, fenfluroxystroburin, fenfluroxystroburin, fenfluroxystroburin, fenfluroxystroburin, fenfluroxystroburin, Bordeaux mixture, copper oxide, mancozeb. Quinoline copper, phthalimide, chlorpyrifos, isoprothiolane, chlorpyrifos, methyl thiophanate, thiamethoxam, benomyl, blasticidin-S, chloroneb, chlorothalonil, cycloflufenoxam, cymoxanil, cyclobutrifluram, diclocymet, diclomezine, dicloran, diethofencarb, dimethomorph, flumorph, dithianon, ethaboxam, etridiazole, oxadixyl, imidacloprid Amidone, fenoxanil, ferimzone, fluazinam, flumetylsulforim, fluopicolide, fluoxytioconazole, flusulfamide, fluazinam, fosetyl-aluminium, hymexazol, propineb, cyazofamid, methisulfocarb, benomyl, pencycuron n), phthalide, polyoxins, propamocarb, pyraclostrobin, proquinazid, pyroquilon, pyriofenone, quinoxal, pentachloronitrobenzene, thiamethoxam, triazoxide, tricyclazole, pyrazosulfan, valamid, zoxamide, mandipropamid, flubendiamide, isopyrazam, sedaxane, benzo[unspecified]flubenzuron, fluoxastrobin, benzo[unspecified]hydroxylamine,3-Difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3',4',5'-trifluoro-biphenyl-2-yl)-amide, isoflucypram, isothiazamine, dipymetitrone, 6-ethyl-5,7-dioxo-pyrrolo[4,5][1,4]dithiacino[1,2-c]isothiazolyl-3-carboxylonitrile, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-indane-4-yl]pyridine-3-carboxamide, 4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazin-3-carboxylonitrile, (R)-3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindane] [-4-yl]pyrazole-4-carboxamide, 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazole-3-amine, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, fluindapyr, coumethoxystrobin, lvbenmixianan, dichlobentiazox, mandestrobin, 3-(4,4-difluoro-3,4-dihydro-3, 3-Dimethylisoquinoline-1-yl)quinolone, 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolinyl)oxy]phenyl]prop-2-ol, oxathiapiprolin, N-[6-[[[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]tert-butyl carbamate, piraziflumid, inpyrfluxam, trolprocarb, chlorfluazuron, 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-formamidin, N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethyl-phenyl]-N-ethyl-N-methyl-formamidin, methanesulfonic acid [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] ester, 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, 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] Tetrazolium-5-one, aminopyrifen, azoxystrobin, indoxazole, fluopyram, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, florylpicoxamid, fenpicoxamid, metarylpicoxamid, isobutylethoxyquin, ipflufenoquin, quinofumelin, isopyram, N-[2-[2,4-dichlorophenoxy]phenyl]-3 -(difluoromethyl)-1-methyl-pyrazole-4-carboxamide, N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide, bensulfuron-methyl, 5-amino-1,3,4-thiadiazole-2-thiol zinc salt (2:1), fluopyram, flufenoxadiazam, fluthiazolinone, fluopyram, pyrapropoyne, picarbutrazox, 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide, 2-(difluoromethyl)-N-((3R)-1, 1,3-Trimethylindim-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, metyltetraprole, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindim-4-yl)pyridine-3-carboxamide, α-(1,1-dimethylethyl)-α-[4'-(trifluoromethoxy)[1,1'-biphenyl]-4-yl]-5-pyrimidinemethanol, fluoxapiprolin, 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, thiabendazole copper, thiamethoxam zinc, amitoline, iprodione, seboctylamine, N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methylformamidin, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methylformamidin, N'-[5-bromo-2-] [Methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methylformamidinium, N'-[5-chloro-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methylformamidinium, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methylformamidinium (these compounds can be prepared by the method described in WO2015 / 155075); N'-[5-bromo-2-methyl-6-methylformamidinium]-N-isopropyl-N-methylformamidinium -(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N-methylformamidinium (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-methylformamidinium, N'-[4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-methoxy-2-methyl-phenyl]-N-isopropyl-N-methylformamidinium (these compounds can be prepared by WO Prepared by the method described in WO 2018 / 228896); N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)oxetane-2-yl]phenyl]-N-methyl-formamidin, N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methyl-formamidin (these compounds can be prepared by 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-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- Fluoroquinoline-3-carboxamide, N-((1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoroquinoline-3-carboxamide, N-((1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoroquinoline-3-carboxamide (these compounds can be prepared by the method described in WO2017 / 153380); 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,5-trifluoro-3,3-dimethylisoquinoline, 1-(6,7-di... Methylpyrazolo[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 derived from WO4) 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-isoquinolinyl)-7,8-dihydro-6H-cyclopentadieno[e]benzimidazole (these compounds can be prepared by the method described in WO 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 1,2,4-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 [Fluoromethyl)-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]isoxazolidin-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 2017 / 055473, WO 2017 / 055469,Prepared by the methods described in WO 2017 / 093348 and WO 2017 / 118689); 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 / 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 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 WO 2017 / 093348 and WO 2017 / 118689); Prepared by the method described in WO 2016 / 156290); 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-propyl]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) (this compound can be prepared by the method described in WO 2014 / 006945); 2,6-dimethyl-1H,5H-[1,4]dithiatino[2,3-c:5,6-c']bipyrrole-1,3,5,7(2H,6H)-tetraone (this compound can be prepared by WO 2016 / 156290); (Prepared by the method described in WO 2011 / 138281); N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]thiobenzamide; N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide; (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide (this compound can be prepared by the method described in WO 2018 / 153707); N'-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidin; N'-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidin (this compound can be prepared by the method described in WO 2011 / 138281); 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 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).

[0063] Most of the active ingredients described above are indicated by what are referred to as “common names” above, with the corresponding “ISO common name” or another “common name” used in different contexts. If the name is not a “common name,” the type of name used is replaced by the name given in parentheses for the specific compound; in this case, the IUPAC name, IUPAC / Chemical Abstracts name, “chemical name,” “traditional name,” “compound name,” or “research code” is used, or if neither of those names nor a “common name” is used, an “alias” is used. “CAS Registry Number” refers to the Chemical Abstracts Registry Number.

[0064] A mixture comprising the compound (A) above, the cyanoacrylate compound, and one or more active ingredients as described above can be applied, for example, as a single "ready-to-use" solution, as a combined spray mixture (consisting of individual formulations of these single active ingredients) (e.g., a "drum mix"), and as a combination of these single active ingredients when applied in a sequential manner (i.e., one after another, such as hours or days). The order in which the compound (A) above, the cyanoacrylate compound, and the active ingredients as described above are applied is not essential for carrying out this invention.

[0065] These compositions of the present invention can also be used for crop enhancement. According to the present invention, 'crop enhancement' means improved plant vigor, improved plant quality, improved tolerance to stress factors, and / or improved input utilization efficiency.

[0066] According to the present invention, 'improvement of plant vigor' means that certain traits are improved in quality or quantity when compared with the same traits of control plants that have been grown under the same conditions but without using the method of the present invention. Such traits include, but are not limited to, earlier and / or improved germination, improved emergence, ability to use fewer seeds, increased root growth, more developed root system, increased root nodulation, increased bud growth, increased tillering, stronger tillering, more productive tillering, increased or improved plant standing, less plant lodging, increased and / or improved plant height, increased plant weight (fresh or dry weight), larger leaves, greener leaf color, increased pigment content, increased photosynthetic activity, earlier flowering, longer panicles, earlier grain maturity, increased seed, fruit, or pod size, increased number of pods or ears, increased number of seeds per pod or ear, increased seed quality, enhanced seed filling, fewer dead basal leaves, delayed wilting, improved plant vigor, increased levels of amino acid compounds in storage tissues, and / or the need for less input (e.g., less fertilizer, water, and / or labor required). Plants with improved vitality may have an increase in any of the above traits or any combination thereof, or in two or more of the above traits.

[0067] According to the present invention, 'improvement of plant quality' means that certain traits are improved in quality or quantity when compared with the same traits of control plants that have been grown under the same conditions but without using the method of the present invention. Such traits include, but are not limited to, improved visual appearance of plants, reduced ethylene (reduced production and / or inhibited reception), improved quality of harvested materials (e.g., seeds, fruits, leaves, vegetables) (such improved quality can manifest as improved visual appearance of harvested materials, improved carbohydrate content (e.g., increased sugar and / or starch content, improved sugar-acid ratio, reduced reducing sugars, increased rate of sugar formation), improved protein content, improved oil content and composition, improved nutritional value, reduced anti-nutritional compounds, improved sensory properties (e.g., improved taste) and / or improved consumer health benefits (e.g., increased vitamin and antioxidant levels)), improved post-harvest characteristics (e.g., enhanced shelf life and / or storage stability, easier processability, easier compound extraction), more uniform crop development (e.g., simultaneous germination, flowering, and / or fruiting of plants) and / or improved seed quality (e.g., for use in subsequent seasons). Plants with improved quality may have increases in any of these traits or any combination thereof, or in two or more of the aforementioned traits.

[0068] According to the present invention, improved tolerance to stress factors means that certain traits are qualitatively or quantitatively improved compared to the same traits in control plants under the same conditions lacking the method of the present invention. Such traits include, but are not limited to, increased tolerance and / or resistance to a variety of abiotic stress factors that induce suboptimal growth conditions, such as drought (e.g., any stress leading to a lack of plant water content, a lack of water absorption potential, or reduced water supply to the plant), cold, heat, osmotic stress, UV stress, flooding, increased salinity (e.g., salinity in the soil), increased mineral exposure, ozone exposure, high light exposure, and / or limited nutrient (e.g., nitrogen and / or phosphorus) utilization. Plants with improved tolerance to stress factors may have increased tolerance to any of the above-described traits or any combination thereof, or to two or more of the above-described traits. In the case of drought and nutrient stress, these improvements in tolerance may be attributed to, for example, more efficient absorption, utilization, or retention of water and nutrients.

[0069] According to the present invention, 'improved input utilization efficiency' means that a plant is able to use a given input level more efficiently than a control plant grown under the same conditions but without using the method of the present invention. Specifically, these inputs include, but are not limited to, fertilizers (such as nitrogen, phosphorus, potassium, and micronutrients), light, and water. Plants with improved input utilization efficiency may have improved use of any of the above-described inputs, or any combination of two or more of the above-described inputs.

[0070] Other crop enhancements of the present invention include reducing plant height or reducing tillering, which are beneficial features in crops or under conditions where less biomass and fewer tillers are desired.

[0071] Any or all of the above crop enhancements can result in improved yields by improving, for example, plant physiology, plant growth and development, and / or plant architecture. In the context of this invention, 'yield' includes, but is not limited to: (i) increases in biomass production, cereal yield, starch content, oil content, and / or protein content, which may result from: (a) an increase in the amount produced by the plant itself or (b) an improved ability to harvest plant material, (ii) improvements in the composition of the harvested material (e.g., improved sugar-acid ratio, improved oil composition, increased nutritional value, reduction of anti-nutritional compounds, increased consumer health benefits) and / or (iii) an increased / facilitated ability to harvest crops, improved crop processability, and / or better storage stability / shelf life. Increased yield of agricultural plants means, where quantitative measurement is possible, a measurably greater yield of a particular product of a particular plant than the yield of the same product produced by that plant under the same conditions (but without the application of this invention). According to the invention, preferably, this yield increase is at least 0.5%, more preferably at least 1%, even more preferably at least 2%, still more preferably at least 4%, preferably 5%, or even higher.

[0072] Any or more crop enhancements can also lead to land use improvements, meaning that land that was previously unusable or suboptimal for planting can become usable. For example, plants that show enhanced survival under drought conditions can be grown in areas with suboptimal rainfall (e.g., perhaps on the edge of a desert or even in the desert itself).

[0073] In one aspect of the invention, crop enhancement is achieved under conditions where stress from pests and / or diseases and / or abiotic stresses is substantially absent. In another aspect of the invention, improvements in plant vigor, stress tolerance, quality, and / or yield are achieved under conditions where stress from pests and / or diseases is substantially absent. For example, pests and / or diseases can be controlled by applying pest-killing treatments before or simultaneously with the methods of the invention. In yet another aspect of the invention, improvements in plant vigor, stress tolerance, quality, and / or yield are achieved under conditions where pest and / or disease stress is absent. In further embodiments, improvements in plant vigor, quality, and / or yield are achieved under conditions where abiotic stresses are absent or substantially absent.

[0074] These compositions of the present invention can also be used in the field of protecting stored goods from fungal attack. According to the invention, the term "stored goods" should be understood to refer to natural substances of plant and / or animal origin and their processed forms, derived from their natural life cycle and intended for long-term protection. Plant-derived stored goods (such as plants or parts thereof (e.g., stems, leaves, tubers, seeds, fruits, or grains)) can be protected in a freshly harvested state or in a processed form (e.g., pre-dried, moistened, crushed, ground, pressed, or baked). Also falling under the definition of stored goods is timber, whether in log form, such as building timber, transmission towers, and fences, or in the form of finished products, such as furniture or objects made of wood. Animal-derived stored goods are hides, leather, fur, hair, etc. The compositions according to the invention can prevent adverse effects such as decay, fading, or mold. Preferably, "stored goods" should be understood to refer to natural substances of plant origin and / or their processed forms, more preferably fruits and their processed forms (e.g., pome, stone fruit, berries, and citrus fruits and their processed forms). In another preferred embodiment of the invention, "stored goods" should be understood to mean timber.

[0075] Therefore, another aspect of the present invention is a method for protecting stored goods, the method comprising applying a composition according to the present invention to the stored goods.

[0076] The compositions of the present invention can also be used in the field of protecting technical materials from fungal attack. According to the present invention, the term "technical material" includes paper; blankets; buildings; cooling and heating systems; wall panels; ventilation and air conditioning systems, etc.; preferably, "technical material" should be understood to refer to wall panels. The compositions according to the present invention can prevent adverse effects such as decay, fading, or mold growth.

[0077] The compositions according to the invention are typically formulated in a variety of ways using formulation aids (such as carriers, solvents, and surfactants). These formulations can be in various physical forms, for example, as powders, gels, wettable powders, water-dispersible granules, water-dispersible tablets, effervescent compressed tablets, emulsifiable concentrates, microemulsifiable concentrates, oil-in-water emulsions, flowable oils, aqueous dispersions, oily dispersions, suspensions, capsule suspensions, emulsifiable granules, soluble liquids, water-soluble concentrates (using water or water-miscible organic solvents as carriers), impregnated polymer films, or in other known forms, such as those described in the Manual on Development and Use of FAO and WHO Specifications for Pesticides, United Nations, First Edition, Second Revision (2010). Such formulations can be used directly or diluted before use. It can be diluted with, for example, water, liquid fertilizer, micronutrients, biological organisms, oil or solvents.

[0078] These formulations can be prepared, for example, by mixing the active ingredients with formulation aids to obtain compositions in the form of finely dispersed solids, particles, solutions, dispersions, or emulsions. These active ingredients can also be formulated with other aids, such as finely dispersed solids, mineral oils, plant or animal-derived oils, modified plant or animal-derived oils, organic solvents, water, surfactants, or combinations thereof.

[0079] These active ingredients can also be contained in microcapsules. Microcapsules contain the active ingredient within a porous carrier. This allows the active ingredient to be released into the environment in a controlled amount (e.g., slow release). Microcapsules typically have a diameter of 0.1 to 500 micrometers. They contain an amount of active ingredient that is approximately 25% to 95% by weight of the capsule. These active ingredients can be in the form of a monolithic solid, fine particles in a solid or liquid dispersion, or in a form suitable for solution. The encapsulating membrane can contain, for example, natural or synthetic rubber, cellulose, styrene / butadiene copolymer, polyacrylonitrile, polyacrylate, polyester, polyamide, polyurea, polyurethane, or chemically modified polymers, as well as starch xanthate, or other polymers known to those skilled in the art. Alternatively, very fine microcapsules can be formed in which the active ingredient is contained in a solid matrix of a base substance as finely dispersed particles, but these microcapsules themselves are not encapsulated.

[0080] Formulation aids suitable for preparing formulations according to the present invention are known in themselves. As liquid carriers, the following can be used: water, toluene, xylene, petroleum ether, vegetable oil, acetone, methyl ethyl ketone, cyclohexanone, acid anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone, butylene carbonate, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetate, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol, diethylene glycol rosinate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethyl... Formamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, dipropylene glycol, alkylpyrrolidone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1,1,1-trichloroethane, 2-heptanone, α-pinene, d-limonene, ethyl lactate, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, γ-butyrolactone, glycerol, glyceryl acetate, glyceryl diacetate, glyceryl triacetate, deca-acetate, etc. Hexadecane, hexanediol, isopentyl acetate, isobornyl acetate, isooctane, isophorone, cumene, isopropyl myristate, lactic acid, laurylamine, isopropyl acetone, methoxypropanol, methyl isopentyl ketone, methyl isobutyl ketone, methyl lauryl ketone, methyl octanoate, methyl oleate, dichloromethane, m-xylene, n-hexane, n-octylamine, octadecanoic acid, octylamine acetate, oleic acid, oleyleneamine, o-xylene, phenol, polyethylene glycol, propionic acid, propyl lactate Propylene carbonate, propylene glycol, propylene glycol methyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylenesulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol methyl ether, diethylene glycol methyl ether, methanol, ethanol, isopropanol, and alcohols with higher molecular weights, such as pentanol, tetrahydrofuranol, hexanol, octanol, ethylene glycol, propylene glycol, glycerol, N-methyl-2-pyrrolidone, etc.

[0081] Suitable solid carriers include, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, diatomaceous earth, limestone, calcium carbonate, bentonite, calcium montmorillonite, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, ground walnut shells, lignin, and similar substances.

[0082] Many surfactants can be advantageously used in both solid and liquid formulations, especially those that can be diluted with a carrier before use. Surfactants can be anionic, cationic, nonionic, or polymeric, and they can be used as emulsifiers, wetting agents, suspending agents, or for other purposes. Typical surfactants include, for example, salts of alkyl sulfates, such as diethanolammonium dodecyl sulfate; salts of alkyl aryl sulfonates, such as calcium dodecylbenzenesulfonate; alkylphenol / olefin oxide addition products, such as ethoxylated nonylphenol; alcohol / olefin oxide addition products, such as ethoxylated tridecyl alcohol; soaps, such as sodium stearate; salts of alkyl naphthalene sulfonates, such as sodium dibutylnaphthalene sulfonate; salts of dialkyl sulfosuccinates, such as sodium di(2-ethylhexyl)sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary ammonium, such as dodecyltrimethylammonium chloride; polyethylene glycol esters of fatty acids, such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of monoalkyl and dialkyl phosphate esters; and other substances, such as those described in McCutcheon's Detergents and Emulsifiers Annual, MC Publishing. Corp.), Ridgewood, New Jersey (1981).

[0083] Other adjuvants that can be used in formulations for killing harmful organisms include crystallization inhibitors, viscosity modifiers, suspending agents, dyes, antioxidants, foaming agents, light absorbers, mixing aids, defoamers, complexing agents, substances that neutralize or change pH and buffer solutions, corrosion inhibitors, fragrances, humectants, absorption enhancers, micronutrients, plasticizers, flow aids, lubricants, dispersants, thickeners, antifreeze agents, microbial agents, and liquid and solid fertilizers.

[0084] Formulations according to the invention may include additives comprising oils of vegetable or animal origin, mineral oils, alkyl esters of such oils, or mixtures of such oils with oil derivatives. The amount of oil additive in the formulations according to the invention is typically from 0.01% to 10% of the mixture to be applied. For example, the oil additive may be added to the spray can at the desired concentration after the spray mixture has been prepared. Preferred oil additives include mineral oils or vegetable oils, such as rapeseed oil, olive oil, or sunflower oil; emulsified vegetable oils; alkyl esters of vegetable oils, such as methyl derivatives; or animal oils, such as fish oil or tallow. Preferred oil additives include C8-C... 22 Alkyl esters of fatty acids, especially C 12 -C 18Methyl derivatives of fatty acids, such as methyl esters of lauric acid, palmitic acid, and oleic acid (methyl laurate, methyl palmitate, and methyl oleate, respectively). Many oil derivatives are known from the Compendium of Herbicide Adjuvants, 10th edition, Southern Illinois University, 2010.

[0085] These formulations typically contain, by weight, from 0.1% to 99%, particularly from 0.1% to 95% of the compounds of components (A) and (B), and by weight, from 1% to 99.9% of formulation aids, which preferably include, by weight, from 0% to 25% of surfactants. Commercial products may preferably be formulated as concentrates, while end users will typically use diluted formulations.

[0086] Application rates vary widely and depend on soil properties, application method, crop species, pests to be controlled, primary climatic conditions, and other factors governed by application method, application time, and target crop. Generally, compounds can be applied at rates ranging from 1 l / ha to 2000 l / ha, particularly from 10 l / ha to 1000 l / ha.

[0087] Certain mixture compositions according to the present invention can exhibit synergistic effects. A synergistic effect exists as long as the combined effect of the active ingredients is greater than the sum of the effects of the individual components. The combined toxicity of the two agents can be assessed using the co-toxicity coefficient (CTC) according to the Sun-YP method (Yun-Pei, Sun. "Toxicity Index - An Improved Method of Comparing the Relative Toxicity of Insecticides." Journal of Economic Entomology 1(1950):45-53.). A CTC value less than 80 indicates an antagonistic effect, a CTC value between 80 and 120 indicates an additive effect, and a CTC value greater than or equal to 120 indicates a synergistic effect.

[0088] CTC = (ATI / TTI) * 100

[0089] Component A represents standard AI, and component B represents the component to be mixed with standard AI.

[0090] ATI (Measured Toxicity Index of the Mixture) = (EC50 of Standard AI) 50 / Mixed EC 50 )*100

[0091] TTI (Theoretical Toxicity Index of the Mixture) = (TI A *P A +TI B *P B )*100

[0092] TI A (Toxicity index of component A) = EC5 of component A 50 EC of component A 50

[0093] P A Percentage of component A in the mixture

[0094] TI B (Toxicity index of component B) = EC5 of component A 50 EC of component B 50

[0095] P B Percentage of component B in the mixture

[0096] However, in addition to the actual synergistic effect relative to the fungicidal activity, the compositions according to the invention may also have other unexpectedly advantageous properties. Examples of such advantageous properties that may be mentioned are: more favorable degradability; improved toxicological and / or ecotoxicological behavior; or improved characteristics of useful plants, including: emergence, crop yield, more developed root system, increased tillering, increased plant height, larger leaves, less basal leaf mortality, stronger tillering, greener leaf color, less fertilizer required, less seed required, more productive tillering, earlier flowering, earlier grain maturity, less verse lodging, increased bud growth, improved plant vigor, and earlier germination.

[0097] The compositions according to the invention can be applied to plant pathogenic microorganisms, useful plants threatened by microbial attack, their sites, their propagation materials, stored goods or technical materials.

[0098] The composition according to the invention can be applied before or after useful plants, their propagation materials, stored goods or technical materials are infected by microorganisms.

[0099] The amount of the composition according to the invention to be applied will depend on various factors, such as the compound used; the object to be treated, such as plants, soil or seeds; the type of treatment, such as spraying, dusting or seed dressing; the purpose of the treatment, such as prevention or treatment; the type of fungus to be controlled or the time of application.

[0100] Typically, when applied to useful plants in combination with component (B) which is typically 1 to 5000 g ai / ha, particularly 2 to 2000 g ai / ha, such as 100, 250, 500, 800, 1000, or 1500 g ai / ha, component (A) is typically applied at a ratio of 5 to 2000 g ai / ha, particularly 10 to 1000 g ai / ha, such as 50, 75, 100, or 200 g ai / ha.

[0101] In agricultural practice, the application rate of the composition according to the invention depends on the type of effect desired and is typically in the range of 20 to 4000 g of total composition per hectare.

[0102] When the composition according to the invention is used to treat seeds, a ratio of 0.001 to 50 g of component (A) compound / kg of seeds, preferably from 0.01 to 10 g / kg of seeds, and 0.001 to 50 g of component (B) compound / kg of seeds, preferably from 0.01 to 10 g / kg of seeds, is generally sufficient.

[0103] To avoid any doubt, when citing references, patent applications, or patents in the text of this application, the full text of the cited references is incorporated herein by reference.

[0104] Example

[0105] The following examples illustrate the invention.

[0106] The composition of the present invention differs from known compositions in that it has greater efficacy at lower application rates, which can be demonstrated by those skilled in the art using the experimental procedures outlined in the examples, with lower application rates (if necessary), such as 50 ppm, 12.5 ppm, 6 ppm, 3 ppm, 1.5 ppm or 0.2 ppm of one or more active ingredients.

[0107] Examples of preparations

[0108]

[0109] The active ingredient is thoroughly mixed with the excipients and the mixture is thoroughly ground in a suitable grinder to provide a wettable powder that can be diluted with water to give a suspension of the desired concentration.

[0110]

[0111] The active ingredient is thoroughly mixed with the adjuvant and the mixture is thoroughly ground in a suitable grinder to provide a powder that can be used directly for seed treatment.

[0112]

[0113] Emulsions with any required dilution that can be used in plant protection can be obtained by diluting such concentrates with water.

[0114]

[0115] A ready-to-use powder is obtained by mixing the active ingredient with a carrier and grinding the mixture in a suitable grinder. This type of powder can also be used for dry seed dressing.

[0116]

[0117]

[0118] The active ingredient and excipients are mixed and ground, and the mixture is moistened with water. The mixture is then extruded and dried in an air stream.

[0119] Coated granules

[0120] Active ingredients [components (A) and (B)] 8%

[0121] Polyethylene glycol (molecular weight 200) 3%

[0122] 89% Kaolin

[0123] The finely ground active ingredient is evenly applied to kaolin clay moistened with polyethylene glycol in a mixer. This process yields dust-free coated granules.

[0124]

[0125] Finely ground active ingredients are tightly mixed with excipients to obtain a suspension concentrate, which can be diluted with water to obtain a suspension of any desired dilution. Using such dilutions, living plants and plant propagation material can be treated and protected from microbial contamination by spraying, watering, or immersion.

[0126]

[0127]

[0128] Finely ground active ingredients are tightly mixed with excipients to obtain a suspension concentrate, which can be diluted with water to obtain a suspension of any desired dilution. Using such dilutions, living plants and plant propagation material can be treated and protected from microbial contamination by spraying, watering, or immersion.

[0129] Sustained-release capsule suspension

[0130] A mixture of 28 parts of the active ingredients [components (A) and (B)] was mixed with 2 parts of an aromatic solvent and 7 parts of a toluene diisocyanate / polymethylene-polyphenyl isocyanate mixture (8:1). This mixture was emulsified in a mixture of 1.2 parts of polyvinyl alcohol, 0.05 parts of an antifoaming agent, and 51.6 parts of water until the desired particle size was achieved. 2.8 parts of a 1,6-hexanediamine mixture in 5.3 parts of water was added to this emulsion. The mixture was stirred until polymerization was complete. The resulting capsule suspension was stabilized by adding 0.25 parts of a thickener and 3 parts of a dispersant. This capsule suspension formulation contained 28% of the active ingredient. The diameter of the medium capsules was 8-15 micrometers. The resulting formulation was applied to seeds as an aqueous suspension in a suitable apparatus for this purpose.

[0131] Biological Example 1

[0132] The fungicidal activity of trifluoropyridine (ISO name N-[(1,2cis)-2-(2,4-dichlorophenyl)cyclobutyl]-2-(trifluoromethyl)pyridine-3-carboxamide), cyazofamid (PHM), and mixtures of trifluoropyridine and PHM in various weight ratios (e.g., 20:1, 10:1, 1:50, and 1:100) against Fusarium effusum was tested.

[0133] The test was conducted according to Pesticides Guidelines for Laboratory Bioactivity Tests, Part 2: Petri Plate Test for Determining Fungicides Inhibition of Mycelial Growth (NY / T 1156.2-2006). Specifically, based on the results of preliminary experiments, the optimal concentration ranges for determining the sensitivity of pathogens to trifluoropyridylamine, PHM, and mixtures thereof were determined, and 5-7 concentration gradients were established so that the inhibition rate of the lowest concentration was close to 10% and the inhibition rate of the highest concentration was close to 90%. Test plates were prepared by adding equal volumes of solutions of trifluoropyridylamine, PHM, and mixtures thereof in DMSO at the desired concentrations to melted PDA medium, and PDA plates with the same volume of DMSO were used as controls.

[0134] Hyphae plugs were prepared at the edges of colonies using a punch with a 5 mm diameter. As the mycelium grew upwards, the plugs were transferred to the center of a PDA medium plate containing trifluoropyridine, PHM, and a mixture thereof, and a control plate. After incubation in the dark at 25°C for three days, the diameter of each mycelial colony on the PDA plate was measured vertically twice and then averaged. Inhibition rate (%) = (Average diameter of mycelial colonies on the control plate - Average diameter of mycelial colonies on the test plate) / (Average diameter of mycelial colonies on the control plate) * 100%.

[0135] EC for each reagent and each mixture was calculated using linear regression analysis between the probability value of the inhibition rate and the logarithm of a series of concentrations. 50 Values. The co-toxicity coefficient (CTC) of the mixture was calculated and evaluated according to the Sun-YP method. The results are shown in Table 1 below.

[0136] Table 1. Effects of trifluoropyridine, PHM, or mixtures thereof on Fusarium sp.

[0137]

[0138] Biological Example 2

[0139] The fungicidal activity of trifluoropyridine, cyazofamid (PHM), and mixtures of trifluoropyridine and PHM in various weight ratios (e.g., 20:1, 10:1, and 1:50) against Fusarium graminearum and Fusarium graminearum was tested.

[0140] The test was conducted according to Pesticides Guidelines for Laboratory Bioactivity Tests, Part 2: Petri Plate Test for Determining Fungicides Inhibition of Mycelial Growth (NY / T 1156.2-2006). Specifically, based on the results of preliminary experiments, the optimal concentration ranges for determining the sensitivity of pathogens to trifluoropyridylamine, PHM, and mixtures thereof were determined, and 5-7 concentration gradients were established so that the inhibition rate of the lowest concentration was close to 10% and the inhibition rate of the highest concentration was close to 90%. Test plates were prepared by adding equal volumes of solutions of trifluoropyridylamine, PHM, and mixtures thereof in DMSO at the desired concentrations to melted PDA medium, and PDA plates with the same volume of DMSO were used as controls.

[0141] Hyphae plugs were prepared at the edges of colonies using a punch with a 5 mm diameter. As the mycelium grew upwards, the plugs were transferred to the center of a PDA medium plate containing trifluoropyridine, PHM, and a mixture thereof, and a control plate. After incubation in the dark at 25°C for three days, the diameter of each mycelial colony on the PDA plate was measured vertically twice and then averaged. Inhibition rate (%) = (Average diameter of mycelial colonies on the control plate - Average diameter of mycelial colonies on the test plate) / (Average diameter of mycelial colonies on the control plate) * 100%.

[0142] EC for each reagent and each mixture was calculated using linear regression analysis between the probability value of the inhibition rate and the logarithm of a series of concentrations. 50 Values. The co-toxicity coefficient (CTC) of the mixture was calculated and evaluated according to the Sun-YP method. The results are shown in Tables 2 and 3 below.

[0143] Table 2. Effects of trifluoropyridine, PHM, or mixtures thereof on Fusarium oxysporum.

[0144]

[0145] Table 3. Effects of trifluoropyridine, PHM, or mixtures thereof on Fusarium graminearum

[0146]

[0147]

Claims

1. A fungicidal composition comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is N-[(1,2cis)-2-(2,4-dichlorophenyl)cyclobutyl]-2-(trifluoromethyl)pyridine-3-carboxamide; and Component (B) is cyazofamid, wherein the weight ratio of component (A) to component (B) is from 20:1 to 1:

100.

2. The fungicidal composition according to claim 1, wherein, Component (A) comprises (1S,2S) and (1R,2R) enantiomers of the compound, and the ratio of the (1S,2S) enantiomer to the (1R,2R) enantiomer is greater than 4:

1.

3. The fungicidal composition according to claim 1 or claim 2, wherein, Component (A) is a pure (1S,2S) enantiomer.

4. The fungicidal composition according to claim 1, wherein, The weight ratio of component (A) to component (B) is from 20:1 to 1:50 or 1:50 to 1:

100.

5. The fungicidal composition according to claim 1, wherein, The composition further comprises an agriculturally acceptable carrier, and optionally a surfactant and / or formulation aid.

6. A method for controlling or preventing plant pathogenic diseases on useful plants or their propagation material, the method comprising applying a fungicidal composition according to any one of claims 1 to 5 to the useful plants, their sites, or their propagation material.

7. A method for controlling or preventing plant pathogenic fungi on useful plants or their propagation material, the method comprising applying a fungicidal composition according to any one of claims 1 to 5 to the useful plants, their sites, or their propagation material.

8. The method according to claim 6 or 7, wherein, The composition comprising components (A) and (B) is in a single "ready-to-use with water" form, or in the form of a combined spray mixture, or the composition components (A) and (B) are applied in a sequential manner.

9. The method according to claim 6 or 7, wherein, The plant in question is a grain.

10. The method according to claim 6 or 7, wherein, The plant in question is rice.

11. The method according to claim 6, wherein, The plant pathogenic diseases mentioned are wheat scab or rice bakanae disease.

12. The method according to claim 7, wherein, The plant pathogenic fungi cause wheat scab or rice bakanae disease on useful plants or their propagation material.

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