Crystal form of (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine

Abstract

The present invention relates to a novel crystalline form of (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine according to formula (I), a method for its preparation, an agrochemical formulation comprising said novel crystalline form, and its use in plant protection applications, in particular its use as a fungicide. JPEG2025516326000022.jpg68162

Description

Technical Field

[0001] The present invention relates to a novel crystalline form of (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine according to formula (I), a method for its preparation, an agrochemical formulation comprising said novel crystalline form B, and its use in plant protection applications, in particular its use as a fungicide.

[0002]

Chemical Formula

[0003] (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine and a method for its preparation are known from WO 2020 / 127780. By methods known from the prior art, (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine is obtained as an amorphous solid.

Background Art

[0004] Polymorphism is the ability of a compound to crystallize in different crystal phases having different arrangements and / or conformations of molecules in the crystal lattice. Thus, polymorphs are different crystalline forms of the same chemical compound. Due to the different arrangements and / or conformations of the molecules, polymorphs can exhibit different physical, chemical and / or biological properties. Properties that can be affected include, but are not limited to, solubility, dissolution rate, stability, optical and mechanical properties, among others. The relative stability of a polymorph depends on its free energy, i.e., the more stable polymorph has a lower free energy. Under a defined set of experimental conditions, only one polymorph has the lowest free energy. This polymorph is the thermodynamically stable form, and all other polymorphs are called metastable forms. Metastable forms are thermodynamically unstable, but nevertheless can be prepared, isolated and analyzed as a result of their relatively slow rate of conversion.

[0005] The generation of different polymorphic forms (also referred to herein as polymorphs or crystal forms) of an active substance is critically important not only for the development of formulations containing the active substance, but also for manufacture on an industrial scale, since unwanted phase changes can lead to thickening and solidification of the formulation and / or to large crystals that can cause clogging in spraying nozzles in spraying devices, such as agricultural spraying machines. Thus, the presence of crystal modifications and knowledge of these properties are highly relevant. Each polymorph is characterized by a specific uniform packing and arrangement of molecules in the solid state. Nevertheless, whether a given chemical compound forms polymorphs at all and if so which ones, and what physical and biological properties the different polymorphs can have, are generally not predictable.

[0006] In addition, pseudopolymorphs called hydrates or solvates can occur. A solvate is a crystalline molecular compound in which the solvent molecules of crystallization are incorporated into a host lattice consisting of unsolvated molecules. A hydrate is a special case of a solvate where the incorporated solvent is water. The presence of solvent molecules within the crystal lattice affects intermolecular interactions and imparts physical properties unique to each solvate. Thus, solvates have their own characteristic values of internal energy, enthalpy, entropy, Gibbs free energy, and thermodynamic behavior.

Brief Description of the Drawings

[0007]

Figure 1a

Figure 1b

Figure 1c

Figure 2a

Figure 3a

Disclosure of the Invention

[0008] In one embodiment, the present invention relates to a novel crystalline form B of (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine according to formula (I).

[0009]

Chemical formula

[0010] By the method according to International Publication No. WO 2020 / 127780, (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine is obtained as an undesirable amorphous form.

[0011] Therefore, an object of the present invention is to provide polymorphic forms having excellent application properties, particularly excellent physicochemical properties such as high stability in suspension concentrate (SC) formulations.

[0012] The compound of formula (I) crystallizes with two modifications, A and B. Polymorphic forms A and B are enantiotropically related and exhibit a critical transition temperature of 49 °C to 66 °C. This temperature range can be achieved during the formulation process, resulting in a solid-solid conversion from polymorphic form B to polymorphic form A, crystallizing in form B at room temperature, and initiating agglomeration in solid-based formulation types.

[0013] Here, surprisingly, it has been found that polymorphic form B of the compound of formula (I) has excellent properties. Polymorphic form B exhibits improved beneficial properties for the formulation of formulations compared to the amorphous forms known from the prior art. Specifically, polymorphic form B exhibits high dilution stability, specifically high stability in suspension concentrate (SC) formulations such as suspension properties, thereby ensuring the prevention of unwanted conversion to another polymorphic form of the compound of formula (I). Polymorphic transformation is expected to cause instability of SC formulations (J. Weiss et al., J. Am. Oil Chem. Soc. 2008, 85, 501 - 511; D.J. Burgess et al., Int. J. Pharmaceutics, 2014, Vol. 466, 223 - 232), such as aggregation of particles resulting in lower suspension properties. In addition, polymorphic form B surprisingly exhibits high stability in slurry experiments carried out over an extended period of time beyond the transition temperature range. No recrystallization events were observed. The high stability prevents related changes in the above properties and thus ensures the enhancement of the safety and quality of formulations and / or compositions comprising polymorphic form B of the compound of formula (I).

[0014] Polymorphic form B of (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine can be characterized by X-ray powder diffraction based on the respective diffraction patterns recorded using Cu-Kα1 radiation (1.5406 Å) at 25°C. The polymorphic form B according to the present invention exhibits at least 3, often at least 5, particularly at least 7, more particularly at least 10, and in particular all of the reflections cited below as values.

[0015]

Table 1

[0016] Polymorphic form B according to the present invention is further characterized by the X-ray powder diffractogram shown in FIG. 1a.

[0017] Polymorphic form B of the compound of formula (I) is characterized in that the X-ray powder diffractogram using Cu-Kα1 radiation at 25 ° C has at least the following reflections: 20.2, 23.3 and 25.1, preferably at least the following reflections: 20.2, 23.3, 25.1, 14.5 and 19.4, more preferably at least the following reflections: 20.2, 23.3, 25.1, 14.5, 19.4, 23.4 and 10.6.

[0018] (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine polymorphic form B can also be characterized by Raman spectroscopy based on each spectrum recorded at a laser wavelength of 1064 nm and a resolution of 2 cm -1 at 25 ° C. Polymorphic form B according to the present invention shows at least 3, often at least 5, especially at least 7, especially all of the bands cited below as peak maxima.

[0019]

Table 2

[0020] Polymorphic form B of the compound of formula (I) is characterized by the following bands: 98, 112 and 1585, preferably at least the following bands: 98, 112, 1585, 1279 and 2925, more preferably at least the following bands: 98, 112, 1585, 1279, 2925, 688 and 1609.

[0021] (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine polymorphic form B, at 25 °C, using a Universal Diamond ATR instrument and a resolution of 2 cm -1 Infrared spectroscopy based on each spectrum recorded using a resolution of -1 can also be characteristic. Polymorphic form B according to the present invention exhibits all of the bands cited next as peak maxima, at least 3, often at least 5, particularly at least 7.

[0022] [Table 3] JPEG2025516326000010.jpg237161JPEG2025516326000011.jpg57161

[0023] Polymorphic form B of the compound of formula (I) is characterized by the following bands: 1403, 819 and 806, preferably at least the following bands: 1403, 819, 806, 1476 and 1274, more preferably at least the following bands: 1403, 819, 806, 1476, 1274, 1383 and 921.

[0024] In addition to polymorphic form B, one further polymorphic form A (Figure 2a) has been identified and is further characterized as follows.

[0025] In another embodiment, the present invention relates to a novel crystalline form A of (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine of formula (I).

[0026] [Chemical formula]

[0027] (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine Polymorph Form A can be characterized by X-ray powder diffraction based on each diffraction pattern recorded using Cu-Kα1 radiation (1.5406 Å) at 25°C. Polymorph Form A exhibits at least 3, often at least 5, particularly at least 7, more particularly at least 10, and in particular all of the reflections cited below as values.

[0028] [Table 4] JPEG2025516326000014.jpg230161

[0029] Polymorph Form A of the compound of formula (I) is characterized in that the X-ray powder diffractogram using Cu-Kα1 radiation at 25°C has at least the following reflections, each cited as a 2θ value ±0.2°: 16.9, 19.8 and 24.5, preferably at least the following reflections: 16.9, 19.8, 24.5, 14.2 and 24.7, more preferably at least the following reflections: 16.9, 19.8, 24.5, 14.2, 24.7, 20.8 and 21.8, and most preferably at least the following reflections: 16.9, 19.8, 24.5, 14.2, 24.7, 20.8, 21.8, 38.9, 38.3 and 29.5.

[0030] Polymorph Form A is further characterized by the X-ray powder diffractogram shown in Figure 2a.

[0031] The thermodynamic stability of Polymorph Forms A and B is highly complex. Both forms are enantiotropically related at a transition temperature in the range of 49°C to 66°C. Below these temperatures, Polymorph Form B is the thermodynamically stable polymorph. Polymorph Form A recrystallizes at higher temperatures but shows a very rapid transition to Polymorph Form B at lower temperatures.

[0032] In a further embodiment, the present invention a) diluting the compound of formula (I) in a suitable solvent or solvent mixture; b) heating the composition of step a) to a temperature of at least 70 °C; c) cooling the solution from step b) to a temperature below 20 °C; A process for producing polymorphic form B comprising the steps of:

[0033] The chemical preparation of (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine according to formula (I) known from WO 2020 / 127780. In this way, the compound of formula (I) used in step a) can be prepared according to WO 2020 / 127780, which is hereby incorporated by reference in its entirety.

[0034] The compound of formula (I) in step a) can essentially be any known form of (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine. This means that (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine can be used in an amorphous form or a mixture of different polymorphic forms or a mixture comprising an amorphous and one or more different polymorphic forms.

[0035] Suitable solvents or solvent mixtures for diluting and / or suspending the compound of formula (I) in step a) and from which the compound of formula (I) can be used to obtain polymorphic form B in step c) are toluene, tetrahydrofuran, acetone, ethyl acetate, acetonitrile, methanol, ethanol, iso-propanol, N,N-dimethylformamide, 1,4-dioxane or DMSO, preferably toluene, ethanol or 1,4-dioxane.

[0036] (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine solution can also be prepared by transferring the reaction mixture obtained by a chemical reaction containing (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine to the solvent or solvent mixture according to the present invention, if necessary, after removing reagents and / or by-products.

[0037] In step b), the solution or slurry is usually heated to a temperature of at least 70 °C, preferably at least 90 °C. In a preferred embodiment, each solvent or solvent mixture is heated to its boiling point.

[0038] In step c), the solution or slurry is cooled to a temperature below 20 °C, preferably below 0 °C.

[0039] The crystallization of polymorphic form B can be promoted or accelerated by seeding with seeds of form B.

[0040] The isolation of polymorphic form B from the mother liquor is carried out by general techniques known in the field of sugar technology, such as filtration, centrifugation or decantation.

[0041] More specifically, polymorphic form B is isolated from the solvent or solvent mixture by leaving the solution or slurry under the crystallization conditions of step c) until at least 90% by weight of the solvent or solvent mixture has evaporated.

[0042] The isolated polymorphic form B can, if necessary, be washed with any solvent, preferably water or a solvent or a mixture of solvents used for crystallization together with a mixture of a solvent or a solvent mixture and water. The washing step can be repeated if necessary, whereby washing with water often becomes the final washing step. Washing is usually carried out at a temperature below 30 °C, often below 25 °C, especially below 20 °C, and if necessary at 0 °C. In a further optional step, the crystals of polymorphic form B can be dried and then subjected to further processing.

[0043] By the crystallization according to the invention, polymorphic form B of (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine is obtained in at least 85%, especially 90%, most preferably at least ≧95%.

[0044] Accordingly, a particular embodiment of the invention relates to (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine, which consists of at least 85%, often at least 90%, or at least ≧95% of polymorphic form B.

[0045] In a further embodiment, the invention relates to a plant protection agent in the form of a conventional formulation comprising polymorphic form B of (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine.

[0046] In a preferred embodiment of the invention, the plant protection agent comprises more than 90% by weight, preferably more than 95% by weight, of polymorphic form B of the compound of formula (I) with respect to the total amount of all forms of the compound of formula (I) present in the composition.

[0047] Here, surprisingly, polymorph B has been found to have improved handling and formulation properties, such as high stability of SC formulations, especially high dilution stability, especially high suspension properties, even at temperatures above the transition temperature range, especially at higher temperatures. Thus, in a further embodiment, the present invention relates to the use of polymorph B of the compound of formula (I) for the manufacture of a formulation having high stability, preferably high dilution stability, more preferably high suspension properties, especially at temperatures above the transition temperature range.

[0048] Use In a further embodiment, the present invention relates to the use of polymorph B of the compound of formula (I) for controlling unwanted microorganisms, preferably unwanted fungi and viruses. In certain embodiments, the present invention relates to controlling unwanted fungi in plants. In certain embodiments of the present invention, the useful plants are transgenic plants.

[0049] In a further embodiment, the present invention relates to a method for controlling unwanted microorganisms, the method comprising spraying a plant with polymorph B as defined above or a plant protection agent comprising polymorph B.

[0050] The compounds and compositions of the present invention have strong bactericidal activity and / or plant defense regulatory ability. They can be used to control unwanted microorganisms such as unwanted fungi and viruses in plants. They can be particularly useful for crop protection (controlling microorganisms causing plant diseases) or for protecting materials (e.g., industrial materials, timber, stored products), as will be described in more detail below. More specifically, the compounds and compositions of the present invention can be used to protect seeds, germinating seeds, sprouted seedlings, plants, plant parts, fruits, harvested products, and / or the soil in which the plants grow from unwanted microorganisms.

[0051] As used herein, controlling or to control includes protecting against, treating, and eradicating unwanted microorganisms. Unwanted microorganisms can be pathogenic viruses or pathogenic fungi, more particularly phytopathogenic viruses, or phytopathogenic fungi. As detailed below, these phytopathogenic microorganisms are the causative agents of a wide range of plant diseases.

[0052] More particularly, the compounds and compositions of the present invention can be used as fungicides. For the purposes of this specification, the term "fungicide" represents a compound or composition that can be used in crop protection to control unwanted fungi such as Plasmodiophoromycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes, and Deuteromycetes.

[0053] The compounds and compositions of the present invention may be used as antiviral agents in crop protection. For example, the compounds and compositions of the present invention may be used against diseases caused by plant viruses such as Tobacco mosaic virus (TMV), Tobacco streak virus, Tobacco stunt virus (TStuV), Tobacco leaf curl virus (VLCV), Tobacco nervilia mosaic virus (TVBMV), Tobacco esca wilt virus (TNDV), Tobacco streak virus (TSV), Potato virus X (PVX), Potato virus Y, S, M, and A, Potato acuba mosaic virus (PAMV), Potato mop-top virus (PMTV), Potato leafroll virus (PLRV), Alfalfa mosaic virus (AMV), Cucumber mosaic virus (CMV), Cucumber green mottle mosaic virus (CGMMV), Cucumber yellow virus (CuYV), Watermelon mosaic virus (WMV), Tomato spotted wilt virus (TSWV), Tomato ringspot virus (TomRSV), Sugarcane mosaic virus (SCMV), Rice dwarf virus, Rice stripe virus, Rice black-streaked dwarf virus, Strawberry mottle virus (SMoV), Strawberry vein banding virus (SVBV), Strawberry mild yellow edge virus (SMYEV), Strawberry crinkle virus (SCrV), Broad bean wilt virus (BBWV), and Melon necrotic spot virus (MNSV).

[0054] The present invention also relates to a method for controlling unwanted microorganisms such as unwanted fungi on plants, comprising the step of spraying the polymorphic form B of the compound of formula (I) of the present invention or at least one composition of the present invention onto the microorganisms and / or their habitats (plants, plant parts, seeds, fruits, or the soil in which the plants grow).

[0055] Typically, when the compounds and compositions of the present invention are used in a curative or protective method for controlling phytopathogenic fungi, their effective and plant-compatible amounts are applied to plants, plant parts, fruits, seeds, or the soil or substrate in which the plants grow. Suitable substrates that may be used for cultivating plants include inorganic-based substrates such as mineral wool, particularly stone wool, perlite, sand or gravel, organic substrates such as peat, pine bark, or sawdust, and petroleum-based substrates such as polymer foam or plastic beads. The effective and plant-compatible amounts are amounts sufficient to control or destroy fungi present or likely to appear in agricultural land and that do not involve significant symptoms of phytotoxicity to the said crops. Such amounts can vary within a wide range depending on the fungi to be controlled, the type of crop, the growth stage of the crop, the climatic conditions and the respective compounds or compositions of the present invention used. This amount can be determined by systematic field trials within the capabilities of those skilled in the art.

[0056] Plants and plant parts The compounds and compositions of the present invention may be applied to any plant or plant part.

[0057] Plants mean all plants and plant populations, such as desirable and undesirable wild plants or crop plants (including natural crop plants). Crops are plants that can be obtained by conventional breeding and optimization methods, or by biotechnology and genetic engineering methods, or a combination of these methods, and include genetically modified plants (GMOs or transgenic plants), as well as plant cultivars that can and cannot be protected by plant breeder's rights.

[0058] Plant cultivars are understood to mean plants having new characteristics ("traits") obtained by conventional breeding, mutagenesis or recombinant DNA techniques. They can be varieties, variants, biotypes, or genotypes.

[0059] Plant parts are understood to mean all parts and organs of plants, above and below ground, such as shoots, leaves, conifers, stalks, stems, flowers, fruiting bodies, fruits, seeds, roots, tubers, and rhizomes. Plant parts also include harvested materials, plant materials, and reproductive propagation materials, such as cuttings, tubers, rhizomes, slips, and seeds.

[0060] Plants and plant parts The compounds and compositions of the present invention can be applied to any plant or plant part.

[0061] Plants mean all plants and plant populations, such as desirable and undesirable wild plants or crop plants (including naturally occurring crop plants). Crops are plants that can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods, or combinations of these methods, including genetically modified plants (GMOs or transgenic plants), as well as plant cultivars that can and cannot be protected by plant breeder's rights.

[0062] Plant cultivars are understood to mean plants having new characteristics ("traits") obtained by conventional breeding, mutagenesis, or recombinant DNA technology. They can be varieties, variants, biotypes, or genotypes.

[0063] Plant parts are understood to mean all parts and organs of plants, above and below ground, such as shoots, leaves, conifers, stalks, stems, flowers, fruiting bodies, fruits, seeds, roots, tubers, and rhizomes. Plant parts also include harvested materials, plant materials, and reproductive propagation materials, such as cuttings, tubers, rhizomes, slips, and seeds.

[0064] Plants that can be processed by the method of the present invention include the following: cotton, flax, grapes, fruits, vegetables, for example, Rosaceae sp. (such as pome fruits like apples and pears, as well as stone fruits like apricots, cherries, almonds and peaches, and soft fruits like strawberries), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (such as banana plants and plantations), Rubiaceae sp. (such as coffee), Theaceae sp., Sterculiceae sp., Rutaceae sp. (such as lemons, oranges and grapefruits); Solanaceae sp. (such as potatoes and tomatoes), Liliaceae sp., Asteraceae sp. (such as lettuce), Umbelliferae sp., Cruciferae sp., Chenopodiaceae sp., Cucurbitaceae sp. (such as cucumbers), Alliaceae sp. (such as leeks, onions), Papilionaceae sp. (such as peas), etc.; major crops such as Gramineae sp. (such as cereals like maize, lawn grass, wheat, rye, rice, barley, oats, millet and triticale), Asteraceae sp. (such as sunflowers), Brassicaceae sp.)(e.g., white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, Chinese cabbage, kabu cabbage, daikon radish, and rape, mustard spinach, horseradish and cress), Fabacae sp. (e.g., kidney bean, peanut), Papilionaceae sp. (e.g., soybean), Chenopodiaceae sp. (e.g., sugar beet, fodder beet, Swiss chard, beetroot); plants useful for gardens and woodlands and ornamental plants; and genetically modified variants of each of these plants.

[0065] Plants and plant cultivars that can be treated by the methods disclosed above include plants and plant cultivars that are resistant to one or more biotic stresses, i.e., the plants exhibit better defense against animal and microbial pests such as nematodes, insects, mites, phytopathogenic fungi, bacterial viruses and / or viroids.

[0066] Plants and plant cultivars that may be treated by the methods disclosed above include plants that are resistant to one or more abiotic stresses. Abiotic stress conditions include, for example, drought, cold exposure, heat exposure, osmotic stress, flooding, increased soil salinity, increased mineral exposure, ozone exposure, high light exposure, limited availability of nitrogen nutrients, limited availability of phosphorus nutrients, and shade avoidance.

[0067] Plants and plant cultivars that can be processed by the methods disclosed above include plants characterized by improved yield characteristics. The increased yield in said plants can be the result of improvements in plant physiological functions, growth, and development, such as, for example, improvements in water use efficiency, water retention efficiency, nitrogen utilization, carbon assimilation, photosynthesis, germination efficiency, and acceleration of maturation. Furthermore, yield can be affected by an improved plant architecture (under stress and non-stress conditions), and includes early flowering, flowering control for hybrid seed production, seedling vigor, plant size, number and distance between internodes, root growth, seed size, fruit size, sheath size, number of sheaths or spikes, number of seeds per pod or spike, seed mass, enhanced seed filling, reduced seed dispersal, sheath splitting, and reduced lodging resistance, but is not limited thereto. Further yield traits include seed composition such as carbohydrate content and composition such as cotton or starch, protein content, oil content and composition, nutritional value, reduction of anti-nutritional compounds, improved processability, and better storage stability.

[0068] Plants and plant cultivars that can be processed by the methods disclosed above include hybrid plants and plant cultivars that already exhibit the characteristics of hybrid vigor or hybrid vitality, which generally result in higher yields, vigor, health, and resistance to biotic and abiotic stresses.

[0069] Transgenic Plants, Seed Treatments, and Integration Events Polymorphic form B of the compound of formula (I) according to the present invention can be advantageously used for treating transgenic plants, plant cultivars or plant parts that have received genetic material conferring advantageous and / or useful traits (characteristics) to these plants, plant cultivars or plant parts. Thus, the present invention is intended to be combinable with one or more recombinant traits or transgenic events, or combinations thereof. For the purposes of this application, transgenic events are created by the insertion of a specific recombinant DNA molecule into a specific location (locus) within the chromosome of the plant genome. The insertion creates a novel DNA sequence called an "event", characterized by the inserted recombinant DNA molecule and a certain amount of genomic DNA in the immediate vicinity / adjacent to both ends of the inserted DNA. Such traits or transgenic events include, but are not limited to, disease and pest resistance, water use efficiency, yield performance, drought resistance, seed quality, improvement of nutritional quality, hybrid seed production, and herbicide tolerance. Specific examples of such advantageous / useful characteristics are better plant growth, vigor, stress tolerance, stability, lodging resistance, nutrient uptake, plant nutrition, and / or yield, in particular, improvement of growth, improvement of tolerance to high or low temperatures, improvement of tolerance to drought or water or soil salinity levels, improvement of flowering performance, facilitation of harvesting, acceleration of ripening, increase in yield, high quality and / or improvement of nutritional value of the harvested product, improvement of the storage life and / or processability of the harvested product, and improvement of resistance to animal and microbial pests such as insects, spiders, nematodes, mites, slugs, snails, etc.

[0070] Among the DNA sequences encoding proteins that confer resistance characteristics against such animal and microbial pests, especially insects, in particular, the genetic material derived from Bacillus thuringiensis encoding Bt proteins, which are widely described in the literature and well-known to those skilled in the art, is particularly mentioned. Proteins extracted from bacteria such as Photorhabdus (International Publication Nos. WO97 / 17432 and WO98 / 08932) are also mentioned.In particular, CrylA, CryIAb, CryIAc, CryIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CryIF proteins or their toxic fragments, and further hybrids or combinations thereof, in particular CrylF protein or hybrids derived from CrylF protein (e.g., hybrid CrylA-CrylF protein or its toxic fragment), CrylA type protein or its toxic fragment, preferably CrylAc protein or hybrids derived from CrylAc protein (e.g., hybrid CrylAb CrylAc protein) or CrylAb or Bt2 protein or its toxic fragment, Cry2Ae, Cry2Af or Cry2Ag protein or its toxic fragment, CrylA.105 protein or its toxic fragment, VIP3Aa19 protein, VIP3Aa20 protein, VIP3A protein produced in COT202 or COT203 cotton events, VIP3Aa protein or its toxic fragment described in Estruch et al. (1996), Proc Natl Acad Sci USA. 28;93(11):5389-94, Cry protein as described in WO 2001 / 47952, Tc-protein derived from Photorhabdus (as described in WO 98 / 08932) such as Xenorhabdus (as described in WO 98 / 50427), Serratia (especially derived from S. entomophila) or insecticidal proteins derived from Photorhabdus species strains, i.e., Bt Cry or VIP proteins are mentioned. Also included herein are any of the above-named sequences, in particular any variant or mutant of any one of these proteins in which several amino acids (1-10, preferably 1-5) different from those of the sequence of these toxic fragments, or transit peptides such as plastid transit peptides, or these proteins fused with another protein or peptide.

[0071] Another and particularly emphasized example of such properties is the conferral of resistance to one or more herbicides, such as imidazolinones, sulfonylureas, glyphosate, or phosphinothricin. Among the DNA sequences encoding proteins that confer the property of resistance to specific herbicides in transformed plant cells and plants, in particular, the bar or PAT genes conferring resistance to glufosinate herbicides or Streptomyces coelicolor genes described in WO 2009 / 152359, genes encoding suitable EPSPS (5-enolpyruvylshikimate-3-phosphate synthase) conferring resistance to herbicides targeting EPSPS, in particular herbicides such as glyphosate and its salts, genes encoding glyphosate - n - acetyltransferase, or genes encoding glyphosate oxidoreductase are mentioned. Further suitable herbicide resistance traits include at least one ALS (acetolactate synthase) inhibitor (e.g., WO 2007 / 024782), mutant Arabidopsis ALS / AHAS genes (e.g., US Patent No. 6,855,533), genes encoding 2,4 - D - monooxygenase conferring resistance to 2,4 - D (2,4 - dichlorophenoxyacetic acid), and genes encoding dicamba monooxygenase conferring resistance to dicamba (3,6 - dichloro - 2 - methoxybenzoic acid).

[0072] Another example of such a trait is resistance to one or more phytopathogenic fungi, such as Asian soybean rust. Among the DNA sequences encoding proteins conferring the trait of resistance to such diseases, in particular, genetic material derived from Glycine tomentella, for example, publicly available accession lines PI441001, PI483224, PI583970, PI446958, PI499939, PI505220, PI499933, PI441008, PI505256, or PI446961 described in WO 2019 / 103918 is mentioned.

[0073] A further and particularly emphasized example of such a trait is, for example, an increased resistance to bacteria and / or viruses for systemic acquired resistance (SAR), and is systemin, phytoalexin, elicitor and resistance genes, as well as correspondingly expressed proteins and toxins.

[0074] Particularly useful transgenic events in transgenic plants or plant cultivars that can be preferably processed according to the present invention include the following: event 531 / PV-GHBK04 (cotton, insect control, described in WO 2002 / 040677); event 1143-14A (cotton, insect control, not deposited, described in WO 2006 / 128569); event 1143-51B (cotton, insect control, not deposited, described in WO 2006 / 128570); event 1445 (cotton, herbicide tolerance, not deposited, described in US 2002 / 120964 or WO 2002 / 034946); event 17053 (rice, herbicide tolerance, deposited as PTA-9843, described in WO 2010 / 117737); event 17314 (rice, herbicide tolerance, deposited as PTA-9844, described in WO 2010 / 117735); event 281-24-236 (cotton, insect control-herbicide tolerance, deposited as PTA-6233, described in WO 2005 / 103266 or US 2005 / 216969); event 3006-210-23 (cotton, insect control-herbicide tolerance, deposited as PTA-6233, US Patent Application Publication No. 2007 / 143876 or International Publication No. 2005 / 103266); Event 3272 (maize, quality trait, deposited as PTA-9972, described in International Publication No. 2006 / 098952 or US Patent Application Publication No. 2006 / 230473); Event 33391 (wheat, herbicide tolerance, deposited as PTA-2347, described in International Publication No. 2002 / 027004), Event 40416 (maize, insect control-herbicide tolerance, deposited as ATCC PTA-11508, described in International Publication No. 11 / 075593); Event 43A47 (maize, insect control-herbicide tolerance, deposited as ATCC PTA-11509, described in International Publication No. 2011 / 075595); Event 5307 (maize, insect control, deposited as ATCC PTA-9561, described in International Publication No. 2010 / 077816); Event ASR-368 (bentgrass, herbicide tolerance, deposited as ATCC PTA-4816, described in US Patent Application Publication No. 2006 / 162007 or International Publication 2004 / 053062); Event B16 (maize, herbicide tolerance, not deposited, described in US Patent Application Publication No. 2003 / 126634); Event BPS-CV127-9 (soybean, herbicide tolerance, deposited as NCIMB No. 41603, described in International Publication No. 2010 / 080829); Event BLR1 (rape, restoration of male sterility, deposited as NCIMB 41193, described in International Publication No. 2005 / 074671), Event CE43-67B (cotton, insect control, deposited as DSM ACC2724, described in US Patent Application Publication No. 2009 / 217423 or International Publication No. 2006 / 128573); Event CE44-69D (cotton, insect control, not deposited, described in US Patent Application Publication No. 2010 / 0024077); Event CE44-69D (cotton, insect control, not deposited, described in WO 2006 / 128571); Event CE46-02A (cotton, insect control, not deposited, described in WO 2006 / 128572); Event COT102 (cotton, insect control, not deposited, described in US Patent Application Publication No. 2006 / 130175 or WO 2004 / 039986); Event COT202 (cotton, insect control, not deposited, described in US Patent Application Publication No. 2007 / 067868 or WO 2005 / 054479); Event COT203 (cotton, insect control, not deposited, described in WO 2005 / 054480); Event DAS21606-3 / 1606 (soybean, herbicide tolerance, deposited as PTA-11028, described in WO 2012 / 033794), Event DAS40278 (maize, herbicide tolerance, deposited as ATCC PTA-10244, described in WO 2011 / 022469); Event DAS-44406-6 / pDAB8264.44.06.l (soybean, herbicide tolerance, deposited as PTA-11336, described in WO 2012 / 075426), Event DAS-14536-7 / pDAB8291.45.36.2 (soybean, herbicide tolerance, deposited as PTA-11335, described in WO 2012 / 075429), Event DAS-59122-7 (maize, insect control - herbicide tolerance, deposited as ATCC PTA 11384, described in U.S. Patent Application Publication No. 2006 / 070139; Event DAS-59132 (maize, insect control - herbicide tolerance, not deposited, described in International Publication No. 2009 / 100188); Event DAS68416 (soybean, herbicide tolerance, deposited as ATCC PTA-10442, described in International Publication No. 2011 / 066384 or International Publication No. 2011 / 066360); Event DP-098140-6 (maize, herbicide tolerance, deposited as ATCC PTA-8296, described in U.S. Patent Application Publication No. 2009-137395 or International Publication No. 08 / 112019); Event DP-305423-1 (soybean, quality trait, not deposited, described in U.S. Patent Application Publication No. 2008 / 312082 or International Publication No. 2008 / 054747); Event DP-32138-1 (maize, hybridization system, deposited as ATCC PTA-9158, described in U.S. Patent Application Publication No. 2009 / 0210970 or International Publication No. 2009 / 103049); Event DP-356043-5 (soybean, herbicide tolerance, deposited as ATCC PTA-8287, described in U.S. Patent Application Publication No. 2010 / 0184079 or International Publication No. 2008 / 002872); Event EE-I (eggplant, insect control, not deposited, described in International Publication No. 07 / 091277); Event Fil 17 (maize, herbicide tolerance, deposited as ATCC 209031, described in U.S. Patent Application Publication No. 2006 / 059581 or International Publication No. 98 / 044140); Event FG72 (soybean, herbicide tolerance, deposited as PTA-11041, described in International Publication No. 2011 / 063413), Event GA21 (maize, herbicide tolerance, deposited as ATCC 209033, described in US Patent Application Publication No. 2005 / 086719 or International Publication No. 98 / 044140; event GG25 (maize, herbicide tolerance, deposited as ATCC 209032, described in US Patent Application Publication No. 2005 / 188434 or International Publication No. 98 / 044140); event GHB119 (cotton, insect control - herbicide tolerance, deposited as ATCC PTA - 8398, described in International Publication No. 2008 / 151780); event GHB614 (cotton, herbicide tolerance, deposited as ATCC PTA - 6878, described in US Patent Application Publication No. 2010 / 050282 or W02007 / 017186); event GJ11 (maize, herbicide tolerance, deposited as ATCC 209030, described in US Patent Application Publication No. 2005 / 188434 or International Publication No. 98 / 044140); event GMRZ13 (sugar beet, virus resistance, deposited as NCIMB - 41601, described in International Publication No. 2010 / 076212); event H7 - l (sugar beet, herbicide tolerance, deposited as NCIMB 41158 or NCIMB 41159, described in US Patent Application Publication No. 2004 / 172669 or International Publication No. 2004 / 074492); event JOPLINl (wheat, Disease tolerance, not deposited, described in US Patent Application Publication No. 2008 / 064032; Event LL27 (soybean, herbicide tolerance, deposited as NCIMB41658, described in International Publication No. 2006 / 108674 or US Patent Application Publication No. 2008 / 320616); Event LL55 (soybean, herbicide tolerance, deposited as NCIMB 41660, described in International Publication No. 2006 / 108675 or US Patent Application Publication No. 2008 / 196127); Event LLcotton25 (cotton, herbicide tolerance, deposited as ATCC PTA-3343, described in International Publication No. 2003 / 013224 or US Patent Application Publication No. 2003 / 097687); Event LLRICE06 (rice, herbicide tolerance, deposited as ATCC 203353, described in US Patent No. 6,468,747 or International Publication No. 2000 / 026345); Event LLRice62 (rice, herbicide tolerance, deposited as ATCC 203352, described in International Publication No. 2000 / 026345), Event LLRICE601 (rice, herbicide tolerance, deposited as ATCC PTA-2600, described in US Patent Application Publication No. 2008 / 2289060 or International Publication No. 2000 / 026356); Event LY038 (maize, quality trait, deposited as ATCC PTA-5623, described in US Patent Application Publication No. 2007 / 028322 or International Publication No. 2005 / 061720); Event MIR162 (maize, insect control, deposited as PTA-8166, described in US Patent Application Publication No. 2009 / 300784 or International Publication No. 2007 / 142840); Event MIR604 (maize, insect control, not deposited, described in US Patent Application Publication No. 2008-167456 or International Publication No. 2005 / 103301); Event MON15985 (cotton, insect control, deposited as ATCC PTA-2516, described in US Patent Application Publication No. 2004 / 250317 or International Publication No. 2002 / 100163); Event MON810 (maize, insect control, not deposited, described in US Patent Application Publication No. 2002 / 102582);Event MON863 (maize, insect control, deposited as ATCC PTA-2605, described in International Publication No. WO 2004 / 011601 or US Patent Application Publication No. 2006 / 095986); Event MON87427 (maize, pollination control, deposited as ATCC PTA-7899, described in International Publication No. WO 2011 / 062904); Event MON87460 (maize, stress resistance, deposited as ATCC PTA-8910, described in International Publication No. WO 2009 / 111263 or US Patent Application Publication No. 2011 / 0138504); Event MON87701 (soybean, insect control, deposited as ATCC PTA-8194, described in US Patent Application Publication No. 2009 / 130071 or International Publication No. WO 2009 / 064652); Event MON87705 (soybean, quality trait - herbicide tolerance, deposited as ATCC PTA-9241, described in US Patent Application Publication No. 2010 / 0080887 or International Publication No. WO 2010 / 037016); Event MON87708 (soybean, herbicide tolerance, deposited as ATCC PTA-9670, described in International Publication No. WO 2011 / 034704); Event MON87712 (soybean, yield, deposited as PTA-10296, described in International Publication No. WO 2012 / 051199), Event MON87754 (soybean, quality trait, deposited as ATCC PTA-9385, described in International Publication No. WO 2010 / 024976); Event MON87769 (soybean, quality trait, deposited as ATCC PTA-8911, described in US Patent Application Publication No. 2011 / 0067141 or International Publication No. WO 2009 / 102873); Event MON88017 (maize, insect control - herbicide tolerance, deposited as ATCC PTA-5582, described in US Patent Application Publication No. 2008 / 028482 or International Publication No. 2005 / 059103); Event MON88913 (cotton, herbicide tolerance, deposited as ATCC PTA-4854, described in International Publication No. 2004 / 072235 or US Patent Application Publication No. 2006 / 059590); Event MON88302 (rapeseed, herbicide tolerance, deposited as PTA-10955, described in International Publication No. 2011 / 153186), Event MON88701 (cotton, herbicide tolerance, deposited as PTA-11754, described in International Publication No. 2012 / 134808); Event MON89034 (maize, insect control, deposited as ATCC PTA-7455, described in International Publication No. 07 / 140256 or US Patent Application Publication No. 2008 / 260932); Event MON89788 (soybean, herbicide tolerance, deposited as ATCC PTA-6708, described in US Patent Application Publication No. 2006 / 282915 or International Publication No. 2006 / 130436); Event MSl1 (rapeseed, pollination control - herbicide tolerance, deposited as ATCC PTA-850 or PTA-2485, described in International Publication No. 2001 / 031042); Event MS8 (rapeseed, pollination control - herbicide tolerance, deposited as ATCC PTA-730, described in International Publication No. 2001 / 041558 or US Patent Application Publication No. 2003 / 188347); Event NK603 (maize, herbicide tolerance, deposited as ATCC PTA-2478, described in US Patent Application Publication No. 2007 / 292854); Event PE-7 (rice, insect control, not deposited, described in International Publication No. 2008 / 114282); Event RF3 (rape, pollination control-herbicide tolerance, deposited as ATCC PTA-730, described in International Publication No. 2001 / 041558 or US Patent Application Publication No. 2003 / 188347); Event RT73 (rape, herbicide tolerance, not deposited, described in International Publication No. 2002 / 036831 or US Patent Application Publication No. 2008 / 070260); Event SYHT0H2 / SYN-000H2-5 (soybean, herbicide tolerance, deposited as PTA-11226, described in International Publication No. 2012 / 082548), Event T227-1 (sugar beet, herbicide tolerance, not deposited, described in International Publication No. 2002 / 44407 or US Patent Application Publication No. 2009 / 265817); Event T25 (maize, herbicide tolerance, not deposited, described in US Patent Application Publication No. 2001 / 029014 or International Publication No. 2001 / 051654); Event T304-40 (cotton, insect control-herbicide tolerance, deposited as ATCC PTA-8171, described in US Patent Application Publication No. 2010 / 077501 or International Publication No. 2008 / 122406); Event T342-142 (cotton, insect control, not deposited, described in International Publication No. 2006 / 128568); Event TC1507 (maize, Insect control - herbicide tolerance, not entrusted, described in US Patent Application Publication No. 2005 / 039226 or International Publication No. 2004 / 099447); Event VIP1034 (maize, insect control - herbicide tolerance, deposited as ATCC PTA - 3925, described in International Publication No. 2003 / 052073), Event 32316 (maize, insect control - herbicide tolerance, deposited as PTA - 11507, described in International Publication No. 2011 / 084632), Event 4114 (maize, insect control - herbicide tolerance, deposited as PTA - 11506, described in International Publication No. 2011 / 084621), Event EE - GM3 / FG72 (soybean, herbicide tolerance, ATCC Deposit No. PTA - 11041) may be stacked with Event EE - GM1 / LL27 or Event EE - GM2 / LL55 (described in International Publication No. 2011 / 063413(A2)), Event DAS - 68416 - 4 (soybean, herbicide tolerance, ATCC Deposit No. PTA - 10442, described in International Publication No. 2011 / 066360(Al)), Event DAS - 68416 - 4 (soybean, herbicide tolerance, ATCC Deposit No. PTA - 10442, described in International Publication No. 2011 / 066384(Al)), Event DP - 040416 - 8 (maize, insect control, ATCC Deposit No. PTA - 11508, described in International Publication No. 2011 / 075593(Al)), Event DP - 043A47 - 3 (maize, insect control, ATCC Deposit No. PTA - 11509, described in International Publication No. 2011 / 075595(Al)), Event DP - 004114 - 3 (maize, insect control, ATCC Deposit No. PTA - 11506, described in International Publication No. 2011 / 084621(Al)), Event DP - 032316 - 8 (maize, insect control, ATCC Deposit No. PTA - 11507, described in International Publication No. 2011 / 084632(Al)), Event MON - 88302 - 9 (rapeseed, herbicide tolerance, ATCC Deposit No. PTA - 10955, described in International Publication No. 2011 / 153186(Al)), Event DAS - 21606 - 3 (soybean, Herbicide tolerance, ATCC Deposit No. PTA-11028, described in International Publication No. WO 2012 / 033794 (A2), event MON-87712-4 (soybean, quality trait, ATCC Deposit No. PTA-10296, described in International Publication No. WO 2012 / 051199 (A2)), event DAS-44406-6 (soybean, stacked herbicide tolerance, ATCC Deposit No. PTA-11336, described in International Publication No. WO 2012 / 075426 (A1)), event DAS-14536-7 (soybean, stacked herbicide tolerance, ATCC Deposit No. PTA-11335, described in International Publication No. WO 2012 / 075429 (A1)), event SYN-000H2-5 (soybean, herbicide tolerance, ATCC Deposit No. PTA-11226, described in International Publication No. WO 2012 / 082548 (A2)), event DP-061061-7 (rape, herbicide tolerance, Deposit No. not available, described in International Publication No. WO 2012 / 071039 (A1)), event DP-073496-4 (rape, herbicide tolerance, Deposit No. not available, described in U.S. Patent Application Publication No. 2012 / 131692), event 8264.44.06.1 (soybean, stacked herbicide tolerance, ATCC Deposit No. PTA-11336, described in International Publication No. WO 2012075426 (A2)), event 8291.45.36.2 (soybean, stacked herbicide tolerance, ATCC Deposit No. PTA-11335, described in International Publication No. WO 2012075429 (A2)), event SYHT0H2 (soybean, ATCC Deposit No. PTA-11226, described in International Publication No. WO 2012 / 082548 (A2)), event MON88701 (cotton, ATCC Deposit No. PTA-11754, described in International Publication No. WO 2012 / 134808 (A1)), event KK179-2 (alfalfa, ATCC Deposit No. PTA-11833, described in International Publication No. WO 2013 / 003558 (A1)), event pDAB8264.42.32.1 (soybean, stacked herbicide tolerance, ATCC Deposit No. PTA-11993, described in International Publication No. WO 2013 / 010094 (A1)), event MZDT09Y (maize, ATCC Deposit No. PTA-13025, described in International Publication No. WO 2013 / 012775 (A1)).

[0075] Furthermore, a list of such transgenic events is provided by the United States Department of Agriculture (USDA) Animal and Plant Health Inspection Service (APHIS) and can be viewed on the website, aphis.usda.gov, on the World Wide Web. For the purposes of this application, the state of such list as of the filing date of this application is relevant.

[0076] Genes / events conferring the desired trait in question may be present in combination with each other in transgenic plants. Examples of transgenic plants that may be mentioned are important crop plants such as cereals (wheat, rice, triticale, barley, rye, oats), maize, soybeans, potatoes, sugar beets, sugar cane, tomatoes, peas, other vegetables, cotton, tobacco, oilseed rape, and fruit trees (including apples, pears, citrus fruits, grapes), with particular emphasis on maize, soybeans, wheat, rice, potatoes, cotton, sugar cane, tobacco, and oilseed rape. Particularly emphasized traits are increased plant resistance to insects, arachnids, nematodes, and slugs, and snails, as well as increased plant resistance to one or more herbicides.

[0077] Commercially available examples of such plants, plant parts or plant seeds that may be preferentially processed according to the invention include products such as plant seeds sold or distributed under the trade names GENUITY®, DROUGHTGARD®, SMARTSTAX®, RIB COMPLETE®, ROUNDUP READY®, VT DOUBLE PRO®, VT TRIPLE PRO®, BOLLGARD II®, ROUNDUP READY 2 YIELD®, YIELDGARD®, ROUNDUP READY® 2 XTEND™, INTACTA RR2 PRO®, VISTIVE GOLD®, and / or XTENDFLEX™.

[0078] Pathogen Polymorphic form B of the compound of formula (I) can preferably be used as a fungicide. The diseases include the following:

[0079] Powdery mildew pathogens, such as species of Blumeria, such as Blumeria graminis; species of Leveillula, such as Leveillula taurica; species of Podosphaera, such as Podosphaera leucotricha or Podosphaera xanthii; species of Sphaerotheca, such as Sphaerotheca fuliginea; diseases caused by species of Erysiphe, such as Erysiphe betae and Erysiphe necator; Rust pathogens, such as species of Gymnosporangium, such as Gymnosporangium sabinae, species of Hemileia, such as Hemileia vastatrix, species of Phakopsora (e.g., Phakopsora pachyrhizi or Phakopsora meibomiae), species of Puccinia (e.g., Puccinia recondita, Puccinia graminis, or Puccinia striiformis), species of Uromyces (e.g., Uromyces appendiculatus) diseases; For example, Alternaria species, such as Alternaria solani or Alternaria mali or Alternaria alternata; Cercospora species, such as Cercospora beticola; Cladiosporium species, such as Cladiosporium cucumerinum; Cochliobolus species, such as Cochliobolus sativus (conidia: Drechslera, syn: Helminthosporium) or Cochliobolus miyabeanus; Colletotrichum species, such as Colletotrichum lindemuthanium or Colletotrichum capsica or Colletotrichum acutatum; Cordana species, such as Cordana musae; Corynespora species, such as Corynespora cassiicola; Cycloconium species, such as Cycloconium oleaginum; Diaporthe species, such as Diaporthe citri; Elsinoe species, such as Elsinoe fawcettii; Gloeosporium species, such as Gloeosporium laeticolor; Glomerella species, such as Glomerella cingulata;Guignardia species, such as Guignardia bidwelli; Leptosphaeria species, such as Leptosphaeria maculans; Magnaporthe species, such as Magnaporthe grisea; Marssonina species, such as Marssonina mali; Microdochium species, such as Microdochium nivale; Monilinia species, such as Monilinia laxa; Mycosphaerella species, such as Mycosphaerella graminicola, Mycosphaerella arachidicola or Mycosphaerella fijiensis; Phaeosphaeria species, such as Phaeosphaeria nodorum, Phyllachora species, such as Phyllachora maydis, Pyrenophora species, such as Pyrenophora teres or Pyrenophora tritici repentis; Ramularia species, such as Ramularia collo-cygni or Ramularia areola; Rhynchosporium species, such as Rhynchosporium secalis; Septoria species, such as Septoria apii or Septoria lycopersici;Leaf blight and leaf wilt caused by Setosphaeria species, such as Setosphaeria turcica; Sclerotinia species, such as Sclerotinia sclerotiorum; Stagonospora species, such as Stagonospora nodorum; Stemphylium species, such as Stemphylium vesicarium; Typhula species, such as Typhula incarnata; Venturia species, such as Venturia inaequalis; Root and stem diseases caused by, for example, Corticium species, such as Corticium graminearum; Fusarium species, such as Fusarium oxysporum; Gaeumannomyces species, such as Gaeumannomyces graminis; Marssonina species, such as Marssonina mali; Rhizoctonia species, such as Rhizoctonia solani; Sarocladium species, such as Sarocladium oryzae; Sclerotium species, such as Sclerotium oryzae; Tapesia species, such as Tapesia acuformis; Thielaviopsis species, such as Thielaviopsis basicola; For example, diseases of ears and spikelets (including corn cob) caused by Alternaria species, such as Alternaria spp.; Aspergillus species, such as Aspergillus flavus; Cladosporium species, such as Cladosporium cladosporioides; Claviceps species, such as Claviceps purpurea; Fusarium species, such as Fusarium culmorum; Gibberella species, such as Gibberella zeae; Monographella species, such as Monographella nivalis; Stagnospora species, such as Stagnospora nodorum; Diseases caused by smut fungi, such as Sphacelotheca species, such as Sphacelotheca reiliana; Tilletia species, such as Tilletia caries or Tilletia controversa; Urocystis species, such as Urocystis occulta; Ustilago species, such as Ustilago nuda; For example, fruit rot caused by species of Aspergillus, such as Aspergillus flavus; Botrytis, such as Botrytis cinerea; Monilinia, such as Monilinia laxa; Penicillium, such as Penicillium expansum or Penicillium purpurogenum; Phomopsis, such as Phomopsis viticola; Rhizopus, such as Rhizopus stolonifer; Sclerotinia, such as Sclerotinia sclerotiorum; Verticilium, such as Verticilium alboatrum; For example, Alternaria species, such as Alternaria brassicicola; Aphanomyces species, such as Aphanomyces euteiches; Ascochyta species, such as Ascochyta lentis; Aspergillus species, such as Aspergillus flavus; Cladosporium species, such as Cladosporium herbarum; Cochliobolus species, such as Cochliobolus sativus (conidia: Drechslera, Bipolaris Syn: Helminthosporium); Colletotrichum species, such as Colletotrichum coccodes; Fusarium species, such as Fusarium culmorum; Gibberella species, such as Gibberella zeae; Macrophomina species, such as Macrophomina phaseolina; Microdochium species, such as Microdochium nivale; Monographella species, such as Monographella nivalis; Penicillium species, such as Penicillium expansum; Phoma species, such as Phoma lingam; Phomopsis species, such as Phomopsis sojae; Pyrenophora species, such as Pyrenophora graminea;Seed and soil-borne rot and blight diseases, as well as seedling diseases, caused by Pyricularia species, such as Pyricularia oryzae; Rhizoctonia species, such as Rhizoctonia solani; Rhizopus species, such as Rhizopus oryzae; Sclerotium species, such as Sclerotium rolfsii; Septoria species, such as Septoria nodorum; Typhula species, such as Typhula incarnata; Verticillium species, such as Verticillium dahliae; For example, cankers, galls and witches' broom diseases caused by Nectria species, such as Nectria galligena; For example, wilt diseases caused by Verticillium species, such as Verticillium longisporum; Fusarium species, such as Fusarium oxysporum; For example, leaf, flower and fruit deformations caused by Exobasidium species, such as Exobasidium vexans; Taphrina species, such as Taphrina deformans; For example, diseases in woody plants caused by Esca species, such as Phaeomoniella chlamydospora, Phaeoacremonium aleophilum or Fomitiporia mediterranea; Ganoderma species, such as Ganoderma boninense; For example, diseases of tubers caused by Rhizoctonia species, such as Rhizoctonia solani; Helminthosporium species, such as Helminthosporium solani; Diseases of soybeans: For example, Alternaria leaf spot (Alternaria spec. atrans tenuissima), anthracnose (Colletotrichum gloeosporoides dematium var. truncatum), brown spot (Septoria glycines), Cercospora leaf spot and leaf blight (Cercospora kikuchii), Choanephora leaf blight (Choanephora infundibulifera trispora) (Syn.)) Dactuliophora glycines leaf spot, Peronospora manshurica downy mildew, Drechslera glycini stem blight, Cercospora sojina leaf blight, Leptosphaerulina trifolii leaf spot, Leveillula Taurica powdery mildew, Phyllosticta sojaecola leaf spot, Phomopsis sojae pod and stem blight, Microsphaera diffusa powdery mildew, Pyrenochaeta glycines leaf spot, Rhizoctonia aerial leaf mat, and Rhizoctonia solani web blight, Phakopsora pachyrhizi, Phakopsora meibomiae rust, Sphaceloma glycines scab, Stemphylium botryosum leaf blight, Fusarium virguliforme sudden death syndrome, Corynespora cassiicola target spot. The leaves, stems, pods, and seeds affected by these fungi are also fungal diseases. For example, fungal diseases of the roots and basal parts of the stems caused by Microscopic sclerotium disease (Calonectria crotalariae), Charcoal rot (Macrophomina phaseolina), Red mold or wilting, Root rot, as well as Pod rot and Collar rot (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti), Mycoleptodiscus root rot disease (Mycoleptodiscus terrestris), Neocosmospora (Neocosmospora vasinfecta), Pod blight and Stem blight (Diaporthe phaseolorum), Twig blight (Diaporthe phaseolorum var. caulivora), Leaf blight (Phialophora gregata), Rhizoctonia root rot, Stem rot, and Damping-off disease (Rhizoctonia solani), Sclerotinia stem rot disease (Sclerotinia sclerotiorum), Sclerotinia southern blight (Sclerotinia rolfsii), Thielaviopsis root rot disease (Thielaviopsis basicola).

[0080] Preferably, the present invention relates to the use of polymorphic form B of a compound of formula (I) for controlling the following diseases: powdery mildew pathogens such as Blumeria species, for example Blumeria graminis; Leveillula species, for example Leveillula taurica; Podosphaera species, for example Podosphaera leucotricha or Podosphaera xanthii; Sphaerotheca species, for example Sphaerotheca fuliginea; Erysiphe species, for example Erysiphe betae and Erysiphe necator - caused diseases; rust pathogens such as Gymnosporangium sabinae, Hemileia species, for example Hemileia vastatrix, Phakopsora species, for example Phakopsora pachyrhizi or Phakopsora meibomiae, Puccinia species, for example Puccinia recondita, Puccinia graminis, or Puccinia striiformis, Uromyces species, for example Uromyces appendiculatus - caused diseases; For example, Alternaria species, such as Alternaria solani or Alternaria mali or Alternaria alternata; Cercospora species, such as Cercospora beticola; Cladiosporium species, such as Cladiosporium cucumerinum; Cochliobolus species, such as Cochliobolus sativus (sexual stage: Drechslera, syn: Helminthosporium) or Cochliobolus miyabeanus; Colletotrichum species, such as Colletotrichum lindemuthanium or Colletotrichum capsica or Colletotrichum acutatum; Corynespora species, such as Corynespora cassiicola; Cycloconium species, such as Cycloconium oleaginum; Diaporthe species, such as Diaporthe citri; Elsinoe species, such as Elsinoe fawcettii; Erysiphe species, such as Erysiphe betae; Gloeosporium species, such as Gloeosporium laeticolor; Glomerella species, such as Glomerella cingulata;Guignardia species, such as Guignardia bidwelli; Leptosphaeria species, such as Leptosphaeria maculans; Magnaporthe species, such as Magnaporthe grisea; Marssonina species, such as Marssonina mali; Microdochium species, such as Microdochium nivale; Monilinia species, such as Monilinia laxa; Mycosphaerella species, such as Mycosphaerella graminicola, Mycosphaerella arachidicola or Mycosphaerella fijiensis; Phaeosphaeria species, such as Phaeosphaeria nodorum; Phyllachora species, such as Phyllachora maydis; Pyrenophora species, such as Pyrenophora teres or Pyrenophora tritici repentis; Ramularia species, such as Ramularia collo-cygni or Ramularia areola; Rhynchosporium species, such as Rhynchosporium secalis; Septoria species, such as Septoria apii or Septoria lycopersici;Leaf blight and leaf wilt caused by Setosphaeria species, such as Setosphaeria turcica; Sclerotinia species, such as Sclerotinia sclerotiorum; Stagonospora species, such as Stagonospora nodorum; Stemphylium species, such as Stemphylium vesicarium; Typhula species, such as Typhula incarnata; Venturia species, such as Venturia inaequalis; Root and stem diseases caused by, for example, Corticium species, such as Corticium graminearum; Fusarium species, such as Fusarium oxysporum; Gaeumannomyces species, such as Gaeumannomyces graminis; Marssonina species, such as Marssonina mali; Rhizoctonia species, such as Rhizoctonia solani; Sarocladium species, such as Sarocladium oryzae; Sclerotium species, such as Sclerotium oryzae; Tapesia species, such as Tapesia acuformis; Thielaviopsis species, such as Thielaviopsis basicola; For example, diseases of ears and spikelets (including the cob of maize) caused by Alternaria species, such as Alternaria spp.; Aspergillus species, such as Aspergillus flavus; Cladosporium species, such as Cladosporium cladosporioides; Claviceps species, such as Claviceps purpurea; Fusarium species, such as Fusarium culmorum; Gibberella species, such as Gibberella zeae; Monographella species, such as Monographella nivalis; Stagnospora species, such as Stagnospora nodorum; Diseases caused by smut fungi, such as Sphacelotheca species, such as Sphacelotheca reiliana; Tilletia species, such as Tilletia caries or Tilletia controversa; Urocystis species, such as Urocystis occulta; Ustilago species, such as Ustilago nuda; For example, fruit rot caused by species of Aspergillus, such as Aspergillus flavus; Botrytis, such as Botrytis cinerea; Monilinia, such as Monilinia laxa; Penicillium, such as Penicillium expansum or Penicillium purpurogenum; Phomopsis, such as Phomopsis viticola; Rhizopus, such as Rhizopus stolonifer; Sclerotinia, such as Sclerotinia sclerotiorum; Verticilium, such as Verticilium alboatrum; For example, Alternaria species, such as Alternaria brassicicola; Aphanomyces species, such as Aphanomyces euteiches; Ascochyta species, such as Ascochyta lentis; Aspergillus species, such as Aspergillus flavus; Cladosporium species, such as Cladosporium herbarum; Cochliobolus species, such as Cochliobolus sativus (conidia: Drechslera, Bipolaris Syn: Helminthosporium); Colletotrichum species, such as Colletotrichum coccodes; Fusarium species, such as Fusarium culmorum; Gibberella species, such as Gibberella zeae; Macrophomina species, such as Macrophomina phaseolina; Microdochium species, such as Microdochium nivale; Monographella species, such as Monographella nivalis; Penicillium species, such as Penicillium expansum; Phoma species, such as Phoma lingam; Phomopsis species, such as Phomopsis sojae;Seed and soil-borne rot and wilt diseases, as well as seedling diseases, caused by Pyrenophora species, such as Pyrenophora graminea; Pyricularia species, such as Pyricularia oryzae; Rhizoctonia species, such as Rhizoctonia solani; Rhizopus species, such as Rhizopus oryzae; Sclerotium species, such as Sclerotium rolfsii; Septoria species, such as Septoria nodorum; Typhula species, such as Typhula incarnata; Verticillium species, such as Verticillium dahliae; For example, cankers, galls and witches' broom diseases caused by Nectria species, such as Nectria galligena; For example, wilt diseases caused by Verticillium species, such as Verticillium longisporum; Fusarium species, such as Fusarium oxysporum; For example, leaf, flower and fruit deformations caused by Exobasidium species, such as Exobasidium vexans; Taphrina species, such as Taphrina deformans; For example, diseases in woody plants caused by Esca species, such as Phaeomoniella chlamydospora, Phaeoacremonium aleophilum or Fomitiporia mediterranea; Ganoderma species, such as Ganoderma boninense; For example, diseases of tubers caused by Rhizoctonia species, such as Rhizoctonia solani; Helminthosporium species, such as Helminthosporium solani; Diseases of soybean; For example, Alternaria leaf spot (Alternaria spec. atrans tenuissima), anthracnose (Colletotrichum gloeosporoides dematium var. truncatum), brown spot (Septoria glycines), Cercospora leaf spot and leaf blight (Cercospora kikuchii), Choanephora leaf blight (Choanephora infundibulifera trispora) (Syn.))、 Dactuliophora glycines leaf spot, Peronospora manshurica downy mildew, Drechslera glycini stem blight, Cercospora sojina leaf blight, Leptosphaerulina trifolii leaf spot, Leveillula Taurica powdery mildew, Phyllosticta sojaecola leaf spot, Phomopsis sojae pod and stem blight, Microsphaera diffusa powdery mildew, Pyrenochaeta glycines leaf spot, Rhizoctonia aerial, leaf mass, and Rhizoctonia solani web blight, Phakopsora pachyrhizi, Phakopsora meibomiae rust, Sphaceloma glycines scab, Stemphylium botryosum leaf blight, Fusarium virguliforme sudden death syndrome, Corynespora cassiicola target spot. The leaves, stems, pods, and seeds caused by these are also fungal diseases. For example, fungal diseases of the roots and basal stems caused by Microdochium blotch (Calonectria crotalariae), Charcoal rot (Macrophomina phaseolina), Red mold or wilting, Root rot, as well as Pod rot and Collar rot (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti), Mycoleptodiscus root rot disease (Mycoleptodiscus terrestris), Neocosmospora (Neocosmospora vasinfecta), Pod blight and Stem blight (Diaporthe phaseolorum), Twig blight (Diaporthe phaseolorum var. caulivora), Leaf blight (Phialophora gregata), Rhizoctonia root rot, Stem rot, and Damping-off (Rhizoctonia solani), Sclerotinia stem rot disease (Sclerotinia sclerotiorum), Sclerotinia southern blight (Sclerotinia rolfsii), Thielaviopsis root rot disease (Thielaviopsis basicola).

[0081] More preferably, the present invention relates to the use of polymorphic form B of a compound of formula (I) for controlling the following diseases: powdery mildew pathogens, such as Blumeria species, such as Blumeria graminis; Leveillula species, such as Leveillula taurica; Podosphaera species, such as Podosphaera leucotricha or Podosphaera xanthii; Sphaerotheca species, such as Sphaerotheca fuliginea; Uncinula species, such as Uncinula necator-caused diseases; For example, Alternaria species, such as Alternaria solani or Alternaria mali or Alternaria alternata; Cercospora species, such as Cercospora beticola; Cladiosporium species, such as Cladiosporium cucumerinum; Cochliobolus species, such as Cochliobolus sativus (conidia: Drechslera, syn: Helminthosporium) or Cochliobolus miyabeanus; Colletotrichum species, such as Colletotrichum lindemuthanium or Colletotrichum capsica or Colletotrichum acutatum; Corynespora species, such as Corynespora cassiicola; Cycloconium species, such as Cycloconium oleaginum; Diaporthe species, such as Diaporthe citri; Elsinoe species, such as Elsinoe fawcettii; Gloeosporium species, such as Gloeosporium laeticolor; Glomerella species, such as Glomerella cingulata; Guignardia species, such as Guignardia bidwelli;Leptosphaeria species, e.g., Leptosphaeria maculans; Magnaporthe species, e.g., Magnaporthe grisea; Microdochium species, e.g., Microdochium nivale; Monilinia species, e.g., Monilinia laxa; Mycosphaerella species, e.g., Mycosphaerella graminicola, Mycosphaerella arachidicola or Mycosphaerella fijiensis; Phaeosphaeria species, e.g., Phaeosphaeria nodorum; Phyllachora species, e.g., Phyllachora maydis; Pyrenophora species, e.g., Pyrenophora teres or Pyrenophora tritici repentis; Ramularia species, e.g., Ramularia collo-cygni or Ramularia areola; Rhynchosporium species, e.g., Rhynchosporium secalis; Septoria species, e.g., Septoria apii or Septoria lycopersici; Setosphaeria species, e.g., Setosphaeria turcica; Sclerotinia species, e.g., Sclerotinia sclerotiorum;Leaf blight and leaf blight caused by Stagonospora species, such as Stagonospora nodorum; Stemphylium species, such as Stemphylium vesicarium; Typhula species, such as Typhula incarnata; Venturia species, such as Venturia inaequalis; For example, diseases of roots and stems caused by Corticium species, such as Corticium graminearum; Fusarium species, such as Fusarium oxysporum; Gaeumannomyces species, such as Gaeumannomyces graminis; Marssonina species, such as Marssonina mali; Rhizoctonia species, such as Rhizoctonia solani; Sarocladium species, such as Sarocladium oryzae; Sclerotium species, such as Sclerotium oryzae; Tapesia species, such as Tapesia acuformis; Thielaviopsis species, such as Thielaviopsis basicola; For example, diseases of ears and spikelets (including maize cob) caused by Alternaria species, such as Alternaria spp.; Aspergillus species, such as Aspergillus flavus; Cladosporium species, such as Cladosporium cladosporioides; Claviceps species, such as Claviceps purpurea; Fusarium species, such as Fusarium culmorum; Gibberella species, such as Gibberella zeae; Monographella species, such as Monographella nivalis; Stagnospora species, such as Stagnospora nodorum; For example, fruit rot caused by species of Aspergillus, such as Aspergillus flavus; Botrytis, such as Botrytis cinerea; Monilinia, such as Monilinia laxa; Penicillium, such as Penicillium expansum or Penicillium purpurogenum; Phomopsis, such as Phomopsis viticola; Rhizopus, such as Rhizopus stolonifer; Sclerotinia, such as Sclerotinia sclerotiorum; Verticillium, such as Verticillium alboatrum; For example, Alternaria species, such as Alternaria brassicicola; Aphanomyces species, such as Aphanomyces euteiches; Ascochyta species, such as Ascochyta lentis; Aspergillus species, such as Aspergillus flavus; Cladosporium species, such as Cladosporium herbarum; Cochliobolus species, such as Cochliobolus sativus (conidia: Drechslera, Bipolaris Syn: Helminthosporium); Colletotrichum species, such as Colletotrichum coccodes; Fusarium species, such as Fusarium culmorum; Gibberella species, such as Gibberella zeae; Macrophomina species, such as Macrophomina phaseolina; Microdochium species, such as Microdochium nivale; Monographella species, such as Monographella nivalis; Penicillium species, such as Penicillium expansum; Phoma species, such as Phoma lingam; Phomopsis species, such as Phomopsis sojae; Pyrenophora species, such as Pyrenophora graminea;Seed and soil-borne rot and wilt diseases, and seedling diseases caused by Pyricularia species, such as Pyricularia oryzae; Rhizoctonia species, such as Rhizoctonia solani; Rhizopus species, such as Rhizopus oryzae; Sclerotium species, such as Sclerotium rolfsii; Septoria species, such as Septoria nodorum; Typhula species, such as Typhula incarnata; Verticillium species, such as Verticillium dahliae; Fusarium species, such as Fusarium oxysporum; Diseases of soybean: For example, Alternaria leaf spot (Alternaria spec. atrans tenuissima), anthracnose (Colletotrichum gloeosporoides dematium var. truncatum), brown spot (Septoria glycines), Cercospora leaf spot and leaf blight (Cercospora kikuchii), Choanephora leaf blight (Choanephora infundibulifera trispora) (Syn.)) Dactuliophora glycines leaf spot, Peronospora manshurica downy mildew, Drechslera glycini stem blight, Cercospora sojina leaf blight, Leptosphaerulina trifolii leaf spot, Leveillula Taurica powdery mildew, Phyllosticta sojaecola leaf spot, Phomopsis sojae pod and stem blight, Microsphaera diffusa powdery mildew, Pyrenochaeta glycines leaf spot, Rhizoctonia aerial, leaf mass, and Rhizoctonia solani web blight, Sphaceloma glycines scab, Stemphylium botryosum leaf blight, sudden death syndrome caused by Fusarium virguliforme, Corynespora cassiicola leaf, stem, pod and seed rot are also fungal diseases. For example, fungal diseases of the roots and basal parts of the stems caused by Microscopic Sclerotinia (Calonectria crotalariae), Charcoal Rot (Macrophomina phaseolina), Red Mold or Wilting, Root Rot, as well as Pod Rot and Collar Rot (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti), Mycoleptodiscus Root Rot Disease (Mycoleptodiscus terrestris), Neocosmospora (Neocosmospora vasinfecta), Pod Blight and Stem Blight (Diaporthe phaseolorum), Twig Blight (Diaporthe phaseolorum var. caulivora), Leaf Blight (Phialophora gregata), Rhizoctonia Root Rot, Stem Rot, and Damping-off (Rhizoctonia solani), Sclerotinia Stem Rot Disease (Sclerotinia sclerotiorum), Sclerotinia Southern Blight (Sclerotinia rolfsii), Thielaviopsis Root Rot Disease (Thielaviopsis basicola).

[0082] Most preferably, the present invention relates to the use of polymorphic form B of the compound of formula (I) for controlling the following diseases: Powdery Mildew pathogen, diseases caused by Sphaerotheca species, such as Sphaerotheca fuliginea; For example, leaf blight and leaf wilt diseases caused by Alternaria species, such as Alternaria solani, Alternaria mali, or Alternaria alternata; Cercospora species, such as Cercospora beticola; Colletotrichum species, such as Colletotrichum lindemuthanium, Colletotrichum capsica, or Colletotrichum acutatum; Diaporthe species, such as Diaporthe citri; Phaeosphaeria species, such as Phaeosphaeria nodorum; Pyrenophora species, such as Pyrenophora teres or Pyrenophora tritici repentis; Septoria species, such as Septoria apii or Septoria lycopersici; For example, root and stem diseases caused by Fusarium species, such as Fusarium oxysporum; For example, diseases of ears and cobs (including the cob of maize) caused by Alternaria species, such as Alternaria spp.; Fusarium species, such as Fusarium culmorum; Botrytis species, such as Botrytis cinerea; For example, seed and soil-borne rot and wilt diseases, and seedling diseases caused by Alternaria species, such as Alternaria brassicicola; Colletotrichum species, such as Colletotrichum coccodes; Fusarium species, such as Fusarium culmorum; Pyrenophora species, such as Pyrenophora graminea; Pyricularia species, such as Pyricularia oryzae; Fusarium species, such as Fusarium oxysporum.

[0083] Mycotoxin In addition, polymorphic form B of the compounds of formula (I) and compositions comprising the same may reduce the mycotoxin content in harvested materials and foods and feeds prepared therefrom. Mycotoxins include, in particular, but not limited to, for example, the following fungi: F. acuminatum, F. asiaticum, F. avenaceum, F. crookwellense, F. culmorum, F. graminearum (Gibberella zeae), F. equiseti, F. fujikoroi, F. musarum, F. oxysporum, F. proliferatum, F. poae, F. pseudograminearum, F. sambucinum, F. scirpi, F. semitectum, F. solani, F. sporotrichoides, F. langsethiae, F. subglutinans, F. tricinctum, F. verticillioides and other Fusarium species, and Aspergillus species such as A. flavus, A. parasiticus, A. nomius, A. ochraceus, A. clavatus, A. terreus, A. versicolor, P. verrucosum, P. viridicatum, P. citrinum, P. expansum, P. claviforme, P. roquefortispecies of Penicillium such as Penicillium roqueforti, species of Claviceps such as C. purpurea, C. fusiformis, C. paspali, C. africana, species of Stachybotrys, and deoxynivalenol (DON), nivalenol, 15-Ac-DON, 3-Ac-DON, T2- and HT2-toxins, fumonisins, zearalenone, moniliformin, fusarin, diacetoxyscirpenol (DAS), beauvericin, enniatins, fusaroprolyferin, fusarenol, ochratoxin, patulin, ergot alkaloids, and aflatoxins which can be produced by others.

[0084] Protection of materials The polymorphic form B of the compound of formula (I) and the composition comprising the same may be used for the protection of materials, in particular for the protection of industrial materials against attack and destruction by phytopathogenic fungi.

[0085] In addition, the polymorphic form B of the compound of formula (I) and the composition comprising the same may be used as an antifouling composition, either alone or in combination with other active ingredients.

[0086] In this context, industrial materials are understood to mean inanimate materials manufactured for use in industry. For example, industrial materials to be protected from alteration or destruction by microorganisms can be adhesives, glues, paper, wallpaper, and board / cardboard, textiles, carpets, leather, wood, fibers and tissue paper, paint and plastic products, cooling lubricants, and other products that can be infected or destroyed by microorganisms. Parts of production plants and buildings such as cooling water circuits, cooling systems and heating systems, ventilation units and air conditioning units, which can be impaired by the growth of microorganisms, may also be mentioned within the scope of the materials to be protected. Industrial materials within the scope of the present invention preferably include adhesives, sizing agents, paper and cardboard, leather, wood, paint, cooling lubricants, and transport fluids, more preferably wood.

[0087] Polymorphic form B of the compound of formula (I) and compositions comprising the same may prevent adverse effects such as rotting, decay, discoloration, decolorization, or mold formation.

[0088] In the case of wood treatment, polymorphic form B of the compound of formula (I) and compositions comprising the same may be used against fungal diseases that may grow on or inside the wood.

[0089] Wood means all types of wood species and all types of processed products of this wood for construction purposes, such as solid wood, high-density wood, laminated wood, and plywood. In addition, polymorphic form B of the compound of formula (I) and compositions comprising the same may be used to protect objects in contact with salt water or brackish water, particularly hulls, screens, nets, buildings, mooring systems, and signal systems from fouling.

[0090] Polymorphic form B of the compound of formula (I) and compositions comprising the same may be used to protect stored products. Stored products are understood to mean natural substances or processed products thereof of plant or animal origin for which long-term protection is desired. Stored products of plant origin, such as plants or plant parts such as stems, leaves, tubers, seeds, fruits, grains, etc., may be protected in the freshly harvested state or after processing by (pre-)drying, wetting, grinding, milling, pressing, or roasting. Stored products include unprocessed wood such as construction timber, utility poles, barriers, etc., or wood in the form of finished products such as furniture. Stored products of animal origin are, for example, hides, leather, furs, and hairs. Polymorphic form B of the compound of formula (I) and compositions comprising the same may prevent adverse effects such as rotting, decay, discoloration, decolorization, or mold formation.

[0091] Examples of microorganisms capable of decomposing or altering industrial materials include bacteria, fungi, yeasts, algae, and slime organisms. The polymorphic form B of the compound of formula (I) and the composition comprising the same preferably act against fungi, in particular molds, wood-discoloring and wood-decomposing fungi (Ascomycetes, Basidiomycetes, Deuteromycetes, and Zygomycetes), as well as slime organisms and algae. Examples include microorganisms of the following genera: Alternaria such as Alternaria tenuis; Aspergillus such as Aspergillus niger; Chaetomium such as Chaetomium globosum; Coniophora such as Coniophora puetana; Lentinus such as Lentinus tigrinus; Penicillium such as Penicillium glaucum; Polyporus such as Polyporus versicolor; Aureobasidium such as Aureobasidium pullulans; Sclerophoma such as Sclerophoma pityophila; Trichoderma such as Trichoderma viride; Ophiostoma spp., Ceratocystis spp., Humicola spp., Petriella spp., Trichurus spp., Coriolus spp., Gloeophyllum spp., Pleurotus spp.) Poria spp., Serpula spp., and Tyromyces spp., Cladosporium spp., Paecilomyces spp., Mucor spp., Escherichia genus such as Escherichia coli; Pseudomonas genus such as Pseudomonas aeruginosa; Staphylococcus genus such as Staphylococcus aureus, Candida spp., and Saccharomyces spp. such as Saccharomyces cerevisae. The plant protection agent may additionally comprise one or more further active ingredients such as fungicides, antibacterial agents, acaricides, nematicides, insecticides, static control agents or herbicides. Mixtures with fertilizers, growth regulators, safeners, nitrification inhibitors, semiochemicals, and / or other agriculturally beneficial agents are also possible. This may make it possible to expand the active spectrum and prevent the development of resistance.

[0092] In a further embodiment, the invention relates to a plant protection agent comprising polymorphic form B of the compound of formula (I), which further comprises one or more additional active substances selected from the group consisting of fungicides, insecticides, herbicides, acaricides, safeners and / or plant growth regulators.

[0093] The active compounds specified herein by these general names are known and can be found, for example, in the Pesticide Manual (17th Ed., British Crop Protection Council 2015) or on the Internet (http: / / www.alanwood.net / pesticides).

[0094] Examples of fungicides that can be mixed with the compounds and compositions of the present invention are as follows 1) to 15): 1) Inhibitors of ergosterol biosynthesis, for example, (1.001) cyproconazole, (1.002) difenoconazole, (1.003) epoxiconazole, (1.004) fenbuconazole, (1.005) fenhexamid, (1.006) fenpropidin, (1.007) fenpropimorph, (1.008) fenpyrazamine, (1.009) fluoxastrobin, (1.010) flusilazole, (1.011) flutriafol, (1.012) hexaconazole, (1.013) imazalil, (1.014) imazalil sulfate, (1.015) ipconazole, (1.016) ipfentrifluconazole, (1.017) mefentrifluconazole, (1.018) metconazole, (1.019) myclobutanil, (1.020) paclobutrazol, (1.021) penconazole, (1.022) prochloraz, (1.023) propiconazole, (1.024) prothioconazole, (1.025) pyriproxyfen, (1.026) spiroxamine, (1.027) tebuconazole, (1.028) tetraconazole, (1.029) triadimenol, (1.030) tridemorph, (1.031) triticonazole, (1.032) (1R,2S,5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.033) (1S,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.034) (2R)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.035) (2R)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl] -1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.036) (2R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.037) (2S)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.038) (2S)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.039) (2S)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.040) (R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.041) (S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.042) [3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.043) 1-({(2R,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole, (1.044) 1-({(2S,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2, 4 - Triazole, (1.045) 1 - {[3 - (2 - Chlorophenyl) - 2 - (2,4 - difluorophenyl) oxirane - 2 - yl] methyl} - 1H - 1,2,4 - triazole - 5 - yl thiocyanate, (1.046) 1 - {[rel(2R,3R) - 3 - (2 - Chlorophenyl) - 2 - (2,4 - difluorophenyl) oxirane - 2 - yl] methyl} - 1H - 1,2,4 - triazole - 5 - yl thiocyanate, (1.047) 1 - {[rel(2R,3S) - 3 - (2 - Chlorophenyl) - 2 - (2,4 - difluorophenyl) oxirane - 2 - yl] methyl} - 1H - 1,2,4 - triazole - 5 - yl thiocyanate, (1.048) 2 - [(2R,4R,5R) - 1 - (2,4 - dichlorophenyl) - 5 - hydroxy - 2,6,6 - trimethylheptan - 4 - yl] - 2,4 - dihydro - 3H - 1,2,4 - triazole - 3 - thione, (1.049) 2 - [(2R,4R,5S) - 1 - (2,4 - dichlorophenyl) - 5 - hydroxy - 2,6,6 - trimethylheptan - 4 - yl] - 2,4 - dihydro - 3H - 1,2,4 - triazole - 3 - thione, (1.050) 2 - [(2R,4S,5R) - 1 - (2,4 - dichlorophenyl) - 5 - hydroxy - 2,6,6 - trimethylheptan - 4 - yl] - 2,4 - dihydro - 3H - 1,2,4 - triazole - 3 - thione, (1.051) 2 - [(2R,4S,5S) - 1 - (2,4 - dichlorophenyl) - 5 - hydroxy - 2,6,6 - trimethylheptan - 4 - yl] - 2,4 - dihydro - 3H - 1,2,4 - triazole - 3 - thione, (1.052) 2 - [(2S,4R,5R) - 1 - (2,4 - dichlorophenyl) - 5 - hydroxy - 2,6,6 - trimethylheptan - 4 - yl] - 2,4 - dihydro - 3H - 1,2,4 - triazole - 3 - thione, (1.053) 2 - [(2S,4R,5S) - 1 - (2,4 - dichlorophenyl) - 5 - hydroxy - 2,6,6 - trimethylheptan - 4 - yl] - 2,4 - dihydro - 3H - 1,2,4 - triazole - 3 - thione, (1.054) 2 - [(2S,4S,5R) - 1 - (2,4 - dichlorophenyl) - 5 - hydroxy - 2,6,6 - trimethylheptan - 4 - yl] - 2,4 - dihydro - 3H - 1,2,4 - triazole - 3 - thione, (1.055) 2-[(2S,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.056) 2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,. 6,6-Trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.057) 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, (1.058) 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, (1.059) 2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.060) 2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.061) 2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.062) 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile, (1.063) 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.064) 5-(allylsulfanyl)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.065) 5-(allylsulfanyl)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.066) 5-(allylsulfanyl)-1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.067) Methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propanoate, (1.068) N'-(2,5-dimethyl-4-(2-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide, (1.069) N'-(2-chloro-4-(4-cyanobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, (1.070) N'-(2-chloro-4-(4-methoxybenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, (1.071) N'-(2-chloro-5-methyl-4-phenoxyphenyl)-N-. Ethyl-N-methylimidofomamide, (1.072) N'-(4-benzyl-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide, (1.073) N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylimidofomamide, (1.074) N'-[5-bromo-6-(2,3-dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimidofomamide, (1.075) N'-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidofomamide, (1.076) N'-{5-bromo-2-methyl-6-[(1-propoxypropan-2-yl)oxy]pyridin-3-yl}-N-ethyl-N-methylimidofomamide, (1.077) N'-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidofomamide, (1.078) N'-{5-bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidofomamide, (1.079) N'-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidofomamide, (1.080) N'-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidofomamide, (1.081) N'-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidofomamide, (1.082) N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenylethyl)phenyl]-N-methylimidofomamide (1.083) 4-[(E)-[ethyl(methyl)amino]methyleneamino]-2,5-dimethylbenzoic acid p-tolylmethyl.

[0095] 2) Inhibitors of the respiratory chain in Complex I or II, such as, (2.001) benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2.004) carboxin, (2.005) cyclobutrifluram, (2.006) fluxapyroxad, (2.007) fluindapyr, (2.008) fluopyram, (2.009) flutolanil, (2.010) fluxapyroxad, (2.011) flutriafol, (2.012) ipfencarbazone, (2.013) isfetamid, (2.014) isoflucypram, (2.015) isopyrazam, (2.016) penflufen, (2.017) penthiopyrad, (2.018) pyriofenone, (2.019) pyrapropyzamide, (2.020) pyraziflumid, (2.021) sedaxane, (2.022) difenoconazole (also known as trifloxystrobin), (2.023) 5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazolin-4-amine, (2.024) 5-chloro-N-[2-[1-(4-chlorophenyl)pyrazol-3-yl]oxyethyl]-6-ethyl-pyrimidin-4-amine, (2.025) N-[2-[1-(4-chlorophenyl)pyrazol-3-yl]oxyethyl]quinazolin-4-amine, (2.026) 1,3-dimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide, (2.027) 1,3-dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.028) 1,3-dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.029) 1-methyl-3-(trifluoromethyl)-N-[2’-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide, (2.030) 2-fluoro-6-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)benzamide, (2.031) 3-(Difluoromethyl)-1-methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide, (2.032) 3-(Difluoromethyl)-1-methyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.033) 3-(Difluoromethyl)-N-[(3R)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide, (2.034) 3-(Difluoromethyl)-N-[(3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide, (2.035) N-[(1R,4S)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.036) N-[(1S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.037) N-[1-(2,4-dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.038) N-[rac-(1S,2S)-2-(2,4-dichlorophenyl)cyclobutyl]-2-(trifluoromethyl)nicotinamide.

[0096] 3) Inhibitors of the respiratory chain in complex III, such as, (3.001) ametoctradin, (3.002) amisulbrom, (3.003) azoxystrobin, (3.004) kresoxim-methyl, (3.005) coumoxystrobin, (3.006) cyazofamid, (3.007) simoxystrobin, (3.008) enoxastrobin, (3.009) famoxadone, (3.010) fenamidone, (3.011) fenpicoxamid, (3.012) florpicoxamid, (3.013) fluopicoxystrobin, (3.014) fluoxastrobin, (3.015) kresoxim-methyl, (3.016) mandestrobin, (3.017) metylpicoxamid, (3.018) metominostrobin, (3.019) methyltetraprole, (3.020) orysastrobin, (3.021) picoxystrobin, (3.022) pyraclostrobin, (3.023) pyra-metostrobin, (3.024) pyraoxystrobin, (3.025) trifloxystrobin, (3.026) (2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylvinyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.027) (2E,3Z)-5-{[1-(4-chloro-2-fluorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (3.028) (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (3.029) (2R)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3.030) (2S)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3.031) (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide, (3.032) (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl, (3.(Z)-Methyl 2-(5-cyclopentyl-2-methylphenoxy)-3-methoxyprop-2-enoate, (3.034)(Z)-methyl 3-methoxy-2-[2-methyl-5-(3-propylpyrazol-1-yl)phenoxy]prop-2-enoate, (3.035)(Z)-methyl 3-methoxy-2-[2-methyl-5-[3-(trifluoromethyl)pyrazol-1-yl]phenoxy]prop-2-enoate, (3.036)Methyl {5-[3-(2,4-dimethylphenyl)-1H-pyrazol-1-yl]-2-methylbenzyl}carbamate, (3.037)(2S)-2-[(3-Hydroxy-4-methoxypyridine-2-carbonyl)amino]propanoic acid [rac-2-(4-bromo-7-fluoro-indol-1-yl)-1-methyl-propyl], (3.038)(2S)-2-[(3-Acetoxy-4-methoxypyridine-2-carbonyl)amino]propanoic acid [rac-2-(7-bromo-4-fluoro-indol-1-yl)-1-methyl-propyl], (3.039)(2S)-2-[(3-Hydroxy-4-methoxypyridine-2-carbonyl)amino]propanoic acid [rac-2-(7-bromoindol-1-yl)-1-methyl-propyl], (3.040)(2S)-2-[(3-Hydroxy-4-methoxypyridine-2-carbonyl)amino]propanoic acid [rac-2-(3,5-dichloro-2-pyridyl)-1-methyl-propyl], (3.041)(2S)-2-[(3-Acetoxy-4-methoxypyridine-2-carbonyl)amino]propanoic acid [(1S)-1-[1-(1-naphthyl)cyclopropyl]ethyl], (3.042)(2S)-2-[(3-Hydroxy-4-methoxypyridine-2-carbonyl)amino]propanoic acid [(1S)-1-[1-(1-naphthyl)cyclopropyl]ethyl], (3.043)(2S)-2-[[3-(Acetoxymethoxy)-4-methoxypyridine-2-carbonyl)amino]propanoic acid [(1S)-1-[1-(1-naphthyl)cyclopropyl]ethyl], (3.044) 2-Methylpropanoic acid [2-[[(1S)-2-[(1RS,2SR)-2-(3,5-dichloro-2-pyridyl)-1-methyl-propoxy]-1-methyl-2-oxo-ethyl]carbamoyl]-4-methoxy-3-pyridyl]oxymethyl, (3.045) N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-formamido-2-hydroxybenzamide.

[0097] 4) Inhibitors of mitosis and cell division, such as, (4.001) Carbendazim, (4.002) Diethofencarb, (4.003) Ethaboxam, (4.004) Fluopicolide, (4.005) Fluopyram, (4.006) Metrafenone, (4.007) Penthiopyrad, (4.008) Pyridachlometyl, (4.009) Pyriofenone (Clazafenone), (4.010) Thiabendazole, (4.011) Thiram, (4.012) Zoxamide, (4.013) 3-Chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine, (4.014) 3-Chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine, (4.015) 4-(2-Bromo-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.016) 4-(2-Bromo-4-fluorophenyl)-N-(2-bromo-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.017) 4-(2-Bromo-4-fluorophenyl)-N-(2-bromophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.018) 4-(2-Bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.019) 4-(2-Bromo-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.020) 4-(2-Bromo-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.021) 4-(2-Chloro-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.022) 4-(2-Chloro-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.023) 4-(2-Chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.024) 4-(2-Chloro-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.025) 4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine, (4.026) N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.027) N-(2-bromophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine, (4.028) N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine.

[0098] 5) Compounds capable of having multi-site action, for example, (5.001) Bordeaux mixture, (5.002) captafol, (5.003) captan, (5.004) chlorothalonil, (5.005) copper hydroxide, (5.006) copper naphthenate, (5.007) copper oxide, (5.008) copper oxychloride, (5.009) copper(II) sulfate, (5.010) dithianon, (5.011) dodine, (5.012) folpet, (5.013) mancozeb, (5.014) maneb, (5.015) metiram, (5.016) metiram zinc, (5.017) copper oxine, (5.018) propineb, (5.019) sulfur and sulfur preparations containing calcium polysulfide, (5.020) thiram, (5.021) dinneb, (5.022) dithiram, (5.023) 6-ethyl-5,7-dioxo-6,7-dihydro-5H-pyrrolo[3’,4’:5,6][1,4]dithiino[2,3-c][1,2]thiazole-3-carbonitrile.

[0099] 6) Compounds capable of including host defense, for example, (6.001) acibenzolar-S-methyl, (6.002) fosetyl aluminum, (6.003) fosetyl calcium, (6.004) fosetyl sodium, (6.005) isothianyl, (6.006) phosphorous acid and its salts, (6.007) probenazole, (6.008) thiazinyl.

[0100] 7) Inhibitors of the amino acid and / or protein biosynthesis, for example, (7.001) cyprodinil, (7.002) kasugamycin, (7.003) kasugamycin hydrochloride hydrate, (7.004) oxytetracycline, (7.005) pyrimethanil.

[0101] 8) Inhibitors of ATP production, for example, (8.001) silthiopham.

[0102] 9) Inhibitors of cell wall synthesis, for example, (9.001) benthiavalicarb, (9.002) dimethomorph, (9.003) flumorph, (9.004) iprovalicarb, (9.005) mandipropamid, (9.006) pyrimorph, (9.007) valifenalate, (9.008) (2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one, (9.009) (2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one.

[0103] 10) Inhibitors of lipid synthesis or transport, or membrane synthesis, such as, (10.001) fluoxapiprolin, (10.002) natamycin, (10.003) oxathiapiprolin, (10.004) propamocarb, (10.005) propamocarb hydrochloride, (10.006) propamocarb fosetylate, (10.007) tolclofos-methyl, (10.008) 1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone, (10.009) 1-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone, (10.010) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (10.011) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (10.012) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-fluoro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (10.013) 2-{(5R)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenylmethanesulfonate, (10.014) 2-{(5S)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate, (10.015) 2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl methanesulfonate, (10.016) 3-[2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-1,5-dihydro-2,4-benzodioxepin-6-yl methanesulfonate, (10.017) 9-fluoro-3-[2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-1,5-dihydro-2,4-benzodioxepin-6-yl methanesulfonate, (10.018) 3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-1,5-dihydro-2,4-benzodioxepin-6-yl methanesulfonate, (10.019) 3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-9-fluoro-1,5-dihydro-2,4-benzodioxepin-6-yl methanesulfonate..

[0104] 11) Inhibitors of melanin biosynthesis, for example, (11.001) tolprocarb, (11.002) tricyclazole.

[0105] 12) Inhibitors of nucleic acid synthesis, for example, (12.001) benalaxyl, (12.002) benalaxyl-M (kiralaxyl), (12.003) metalaxyl, (12.004) metalaxyl-M (mefenoxam).

[0106] 13) Inhibitors of signal transduction, for example, (13.001) fluazinam, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazid, (13.005) quinoxyfen, (13.006) vinclozolin.

[0107] 14) Compounds that can act as uncouplers, for example, (14.001) fluazinam, (14.002) meptyldinocap.

[0108] 15) Further compounds, for example, (15.001) abscisic acid, (15.002) aminopyrifen, (15.003) benzothiazole, (15.004) betoxazine, (15.005) capsimycin, (15.006) carbox, (15.007) chinomethionat, (15.008) chloroinnocid, (15.009) coufuraneb, (15.010) cifulfenamide, (15.011) cymoxanil, (15.012) cyprosulfamide, (15.013) dipimetron, (15.014) D-tagatose, (15.015) flufenoxadiazam, (15.016) flumethylsulfonium, (15.017) fluthianil, (15.018) ipflufenoquin (15.019) methyl isothiocyanate, (15.020) mildeomycin, (15.021) nickel dimethyldithiocarbamate, (15.022) nitrothal isopropyl, (15.023) oxyphenthiin, (15.024) pentachlorophenol and salts, (15.025) picarbutrazox, (15.026) quinofumelin, (15.027) tebufloquin, (15.028) tecnazene, (15.029) torufanide, (15.030) 2-(6-benzylpyridin-2-yl)quinazoline, (15.031) 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline, (15.032) 2-phenylphenol and salts, (15.033) 4-amino-5-fluoropyrimidin-2-ol (tautomer: 4-amino-5-fluoropyrimidin-2(1H)-one), (15.034) 4-oxo-4-[(2-phenylethyl)amino]butanoic acid, (15.035) 5-amino-1,3,4-thiadiazole-2-thiol, (15.036) 5-chloro-N'-phenyl-N'-(prop-2-yn-1-yl)thiophene-2-sulfonohydrazide, (15.037) 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidin-4-amine, (15.038) 5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidin-4-amine, (15.039) but-3-yn-1-yl {6-[({[(Z)-(1-methyl-1H-tetrazole- {(5-yl)(phenyl)methylene}amino}oxy)methyl]pyridin-2-yl}carbamate, (15.040)(2Z)-ethyl 3-amino-2-cyano-3-phenylacrylate, (15.041)methyl 2-[acetyl-[2-ethylsulfonyl-4-(trifluoromethyl)benzoyl]amino]-5-(trifluoromethoxy)benzoate, (15.042)N-acetyl-N-[2-bromo-4-(trifluoromethoxy)phenyl]-2-ethylsulfonyl-4-(trifluoromethyl)benzamide, (15.043)phenazine-1-carboxylic acid, (15.044)propyl 3,4,5-trihydroxybenzoate, (15.045)quinolin-8-ol, (15.046)quinolin-8-ol sulfate (2:1), (15.047)(2R)-2-benzyl-N-(8-fluoro-2-methyl-3-quinolyl)-2,4-dimethyl-pentanamide, (15.048)(2S)-2-benzyl-N-(8-fluoro-2-methyl-3-quinolyl)-2,4-dimethyl-pentanamide, (15.049)1-(4,5-dimethyl-1H-benzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.050)1-(4,5-dimethylbenzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline, (15.051)1-(5-(fluoromethyl)-6-methyl-pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.052)1-(5,6-dimethylpyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.053)1-(6-(difluoromethyl)-5-methoxy-pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.054)1-(6-(difluoromethyl)-5-methyl-pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.055)1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline, (15.056) 1-(6,7-Dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.057) 2-{2-Fluoro-6-[(8-fluoro-2-methylquinolin-3-yl)oxy]phenyl}propan-2-ol, (15.058) 3-(4,4,5-Trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline, (15.059) 3-(4,4-Difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)-8-fluoroquinoline, (15.060) 3-(4,4-Difluoro-5,5-dimethyl-4,5-dihydrothieno[2,3-c]pyridin-7-yl)quinoline, (15.061) 3-(5-Fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline, (15.062) 4,4-Difluoro-3,3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline, (15.063) 4,4-Difluoro-3,3-dimethyl-1-(6-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline, (15.064) 5-Bromo-1-(5,6-dimethylpyridin-3-yl)-3,3-dimethyl-3,4-dihydroisoquinoline, (15.065) 7,8-Difluoro-N-[rac-1-benzyl-1,3-dimethyl-butyl]quinoline-3-carboxamide, (15.066) 8-Fluoro-3-(5-fluoro-3,3,4,. (4 - Tetramethyl - 3,4 - dihydroisoquinolin - 1 - yl) - quinoline, (15.067) 8 - Fluoro - 3 - (5 - fluoro - 3,3 - dimethyl - 3,4 - dihydroisoquinolin - 1 - yl) - quinoline, (15.068) 8 - Fluoro - N - (4,4,4 - trifluoro - 2 - methyl - 1 - phenylbutan - 2 - yl) quinoline - 3 - carboxamide, (15.069) 8 - Fluoro - N - [(1R) - 1 - [(3 - fluorophenyl) methyl] - 1,3 - dimethyl - butyl] quinoline - 3 - carboxamide, (15.070) 8 - Fluoro - N - [(1S) - 1 - [(3 - trifluorophenyl) methyl] - 1,3 - dimethyl - butyl] quinoline - 3 - carboxamide, (15.071) 8 - Fluoro - N - [(2S) - 4,4,4 - trifluoro - 2 - methyl - 1 - phenylbutan - 2 - yl] quinoline - 3 - carboxamide, (15.072) 8 - Fluoro - N - [rac - 1 - [(3 - trifluorophenyl) methyl] - 1,3 - dimethyl - butyl] quinoline - 3 - carboxamide, (15.073) 9 - Fluoro - 2,2 - dimethyl - 5 - (quinolin - 3 - yl) - 2,3 - dihydro - 1,4 - benzoxazepine, (15.074) N - (2,4 - dimethyl - 1 - phenylpentan - 2 - yl) - 8 - fluoroquinoline - 3 - carboxamide, (15.075) N - [(1R) - 1 - benzyl - 1,3 - dimethyl - butyl] - 7,8 - difluoro - quinoline - 3 - carboxamide, (15.076) N - [(1S) - 1 - benzyl - 1,3 - dimethyl - butyl] - 7,8 - difluoro - quinoline - 3 - carboxamide, (15.077) N - [(2R) - 2,4 - dimethyl - 1 - phenylpentan - 2 - yl] - 8 - fluoroquinoline - 3 - carboxamide, (15.078) rac - 2 - Benzyl - N - (8 - fluoro - 2 - methyl - 3 - quinolyl) - 2,4 - dimethyl - pentanamide, (15.079) 1,1 - Diethyl - 3 - [[4 - [5 - (trifluoromethyl) - 1,2,4 - oxadiazol - 3 - yl] phenyl] methyl] urea, (15.080) 1,3 - Dimethoxy - 1 - [[4 - [5 - (trifluoromethyl) - 1,2,4 - oxadiazol - 3 - yl] phenyl] methyl] urea, (15.081) 1-[[3-Fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl]methyl]azepan-2-one, (15.082) 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-one, (15.083) 1-methoxy-1-methyl-3-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.084) 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]. Phenyl]methyl]urea, (15.085) 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.086) 2-(difluoromethyl)-5-[2-[1-(2,6-difluorophenyl)cyclopropoxy]pyrimidin-5-yl]-1,3,4-oxadiazole, (15.087) 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide, (15.088) 3,3-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-one, (15.089) 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.090) 4,4-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one, (15.091) 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, (15.092) 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl dimethylcarbamate, (15.093) 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, (15.094) 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[(1R)-1-(2,6-difluorophenyl)ethyl]pyrimidin-2-amine, (15.095) 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[(1R)-1-(2,6-difluorophenyl)propyl]pyrimidin-2-amine, (15.096) 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[(1R)-1-(2-fluorophenyl)ethyl]pyrimidin-2-amine, (15.097) 5-[5-(Difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[(1R)-1-(2-fluorophenyl)ethyl]pyrimidin-2-amine, (15.098) 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[(1R)-1-(3,5-difluorophenyl)ethyl]pyrimidin-2-amine, (15.099) 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[(1R)-1-phenylethyl]pyrimidin-2-amine,. (15.100) 5-[5-(Difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)cyclopropyl]pyrimidin-2-amine, (15.101) 5-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one, (15.102) ethyl 1-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}-1H-pyrazole-4-carboxylate, (15.103) methyl {4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}carbamate, (15.104) N-(1-methylcyclopropyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.105) N-(2,4-difluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.106) N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, (15.107) N,N-dimethyl-1-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}-1H-1,2,4-triazol-3-amine, (15.108) N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.109) N-[(E)-N-methoxy-C-methyl-carboximidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.110) N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.111) N-[(Z)-N-methoxy-C-methyl-carboximidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.112) N-[[2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-3,3,3-trifluoropropanamide, (15.113) N-[[4-[5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, (15.114) N-[4-[5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]cyclopropanecarboxamide, (15.115) N-{2,3-Difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}butanamide, (15.116) N-{4-[5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}cyclopropanecarboxamide, (15.117) N-{4-[5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}propanamide, (15.118) N-Allyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]acetamide, (15.119) N-Allyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, (15.120) N-Ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, (15.121) N-Methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide, (15.122) N-Methyl-4-. [5-(Trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.123) N-Methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide, (15.124) N-Methyl-N-phenyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide.

[0109] All of the named mixed partners of the above classifications (1) to (15) can exist in the form of the free compounds or, where their functional groups permit, in the form of their agrochemically active salts.

[0110] The compounds and compositions of the present invention may be combined with one or more biological control agents.

[0111] As used herein, the term "biological control" is defined as the control of pests such as phytopathogenic fungi and / or insects and / or mites and / or nematodes by the use or adoption of biological control agents.

[0112] As used herein, the term "biological control agent" is defined as an organism other than a harmful organism and / or a protein or secondary metabolite produced by such an organism for biological control. Variants of the second organism shall be included in the definition of biological control agent. The term "variant" refers to a variant of the parent strain, as well as a method for obtaining a variant or variant having greater insecticidal activity than that expressed by the parent strain. The "parent strain" is defined herein as the original strain before mutagenesis. To obtain such variants, the parent strain can be adequately treated with chemicals such as N-methyl-N'-nitro-N-nitrosoguanidine, ethyl methanesulfonate, or by irradiation using gamma rays, X-rays, or UV irradiation, or by other means well known to those skilled in the art. Known mechanisms of biological control agents include enteric bacteria that control root rot by defeating fungi for the space on the root surface. Bacterial toxins such as antibiotics have been used to control pathogens. The toxin can be isolated and applied directly to the plant, or the bacterial species can be administered to produce the toxin in situ.

[0113] A "variant" is a strain having all the identifying characteristics of the NRRL or ATCC deposit number shown in this specification and can be identified as having a genome that hybridizes under high stringency conditions to the genome of the NRRL or ATCC deposit number.

[0114] "Hybridization" refers to a reaction in which one or more polynucleotides react to form a complex that is stabilized through hydrogen bonds between the bases of nucleotide residues. The hydrogen bonds can occur through Watson-Crick base pairing, Hoogstein binding, or other sequence-specific ways. The complex can comprise two strands forming a double-stranded structure, three or more strands forming a multi-stranded complex, a single self-hybridizing strand, or any combination thereof. The hybridization reaction can be carried out under various "stringency" conditions. Generally, a low-stringency hybridization reaction is carried out at about 40 °C in a solution of 10× SSC or equivalent ionic strength / temperature. A hybridization reaction of moderate stringency is typically carried out at about 50 °C in 6× SSC, and a highly stringent hybridization reaction is generally carried out at about 60 °C in 1× SSC.

[0115] Variants with the indicated NRRL or ATCC accession numbers can also be defined as strains having a genomic sequence with greater than 85%, more preferably greater than 90%, or more preferably greater than 95% sequence identity to the genome of the indicated NRRL or ATCC accession number. A polynucleotide or polynucleotide region (or polypeptide or polypeptide region), when aligned, has a certain percentage (e.g., 80%, 85%, 90%, or 95%) of "sequence identity" to another sequencing means in which the percentage of bases (or amino acids) is the same in the comparison of the two sequences. This alignment and percent homology or sequence identity can be determined using software programs known in the art, such as those described in "Current Protocols in Molecular Biology" (F. M. Ausubel et al., eds., 1987).

[0116] NRRL, the abbreviation of Agricultural Research Service Culture Collection, is an international depository institution for the deposit of microbial strains for the purpose of international recognition of the deposit of microorganisms for patent procedures. Its location is at 1815 North University Street, Peoria, Illinois 61604, USA, in the National Center for Agricultural Utilization Research, Agricultural Research Service, United States Department of Agriculture.

[0117] ATCC, the abbreviation of American Type Culture Collection, is an international depository institution for the deposit of microbial strains for the purpose of international recognition of the deposit of microorganisms for patent procedures. Its location is at 10801 University Boulevard, Manassas, Virginia 10110, USA, in the ATCC Patent Depository.

[0118] Examples of biological control agents that may be combined with the compounds and compositions of the present invention are as follows (A) to (G): (A) Antibacterial agents selected from the following groups: (A1)(A1.01) Bacillus subtilis, in particular, strain QST713 / AQ713 (available from Bayer CropScience LP, USA, as SERENADE OPTI or SERENADE ASO, NRRL Deposit No. B21661, US Patent No. 6,060,051); (A1.02) Bacillus sp., in particular, strain D747 (available from Kumiai Chemical Industry Co., Ltd. as DOUBLE NICKEL®), Deposit No. FERM BP-8234, US Patent No. 7,094,592; (A1.03) Bacillus pumilus, in particular, strain BU F-33, NRRL Deposit No. 50185 (available from BASF as part of the CARTISSA® product, European Registration No. 71840-19); (A1.04) Bacillus subtilis var. amyloliquefaciens strain FZB24 Deposit No. DSM 10271 (available from Novozymes as TAEGRO® or TAEGRO®), ECO (EPA Registration No. 70127-5); (A1.05) Paenibacillus sp. strain Deposit No. NRRL B-50972 or Deposit No. NRRL B-67129, International Publication No. 2016 / 154297; (A1.06) Bacillus subtilis strain BU1814, (available from BASF SE as VELONDIS® PLUS, VELONDIS® FLEX and VELONDIS® EXTRA); (A1.07) Bacillus mojavensis strain R3B (Deposit No. NCAIM(P)B001389) (International Publication No. 2013 / 034938), from Certis USA LLC, a subsidiary of Mitsui & Co.; (A1.08) Bacillus subtilis CX-9060, from Certis USA LLC, a subsidiary of Mitsui & Co.; (A1.09) Paenibacillus polymyxa, in particular strain AC-1 (e.g., from TOPSEED®, Green Biotech Company Ltd.); (A1.10) Pseudomonas proradix (e.g., from PRORADIX®, Sourcon Padena); (A1.11) Pantoea agglomerans, in particular strain E325 (Deposit No. NRRL B-21856) (available from Northwest Agri Products as BLOOMTIME BIOLOGICAL™ FD BIOPESTICIDE), and the like bacteria; and. (A2)(A2.01) Aureobasidium pullulans, in particular the budding spores of strain DSM14940, the budding spores of strain DSM 14941 or a mixture of the budding spores of strain DSM14940 and strain DSM14941 (e.g., BOTECTOR®, and BLOSSOM PROTECT® bio-ferm, from Switzerland); (A2.02) Pseudozyma aphidis (disclosed in WO2011 / 151819 (Hebrew University Yissum Research Development Company)); (A2.03) Saccharomyces cerevisiae, in particular strains CNCM No. I-3936, CNCM No. I-3937, CNCM No. I-3938 or CNCM No. I-3939 (International Publication No. 2010 / 086790), Lesaffre et Compagnie, France, and the like fungi; (B) A biocidal fungicide selected from the following group: (B1) Bacteria, for example: (B1.01) Bacillus subtilis, in particular, strain QST713 / AQ713 (available from Bayer CropScience LP, USA, under the name SERENADE OPTI or SERENADE ASO, described in NRRL Deposit No. B21661 and U.S. Patent No. 6,060,051); (B1.02) Bacillus pumilus, in particular, strain QST2808 (available from Bayer CropScience LP, USA, under the name SONATA®, described in Deposit No. NRRL B-30087 and U.S. Patent No. 6,245,551); (B1.03) Bacillus pumilus, in particular, strain GB34 (available from Bayer AG, Germany, under the name Yield Shield®); (B1.04) Bacillus pumilus, in particular, strain BU F-33, NRRL Deposit No. 50185 (available from BASF as part of the CARTISSA product, European Registration No. 71840-19); (B1.05) Bacillus amyloliquefaciens, in particular, strain D747 (available from Kumiai Chemical Industry Co., Ltd. under the name Double Nickel™, Deposit No. FERM BP-8234, U.S. Patent No. 7,094,592); (B1.06) Bacillus subtilis Y1336 (available from Bion-Tech, Taiwan, under the name BIOBAC® WP, registered as a biopesticide in Taiwan under registration numbers 4764, 5454, 5096 and 5277); (B1.07) Bacillus subtilis strain MBI 600 (available from BASF SE under the name SUBTILEX), Deposit No. NRRL B-50595, U.S. Patent No. 5,061,495; (B1.08) Bacillus subtilis strain GB03 (available from Bayer AG, Germany, under the name Kodiak®); (B1.09) Bacillus subtilis var. amyloliquefaciens strain FZB24, Deposit No. DSM. 10271 (available from Novozymes as TAEGRO® or TAEGRO®; ECO (EPA registration No. 70127-5)); (B1.10) Bacillus mycoides isolate J, deposit No. B-30890 (available from Certis USA LLC, a Mitsui & Co. subsidiary, as BMJ TGAI® or WG and LifeGard™); (B1.11) Bacillus licheniformis, particularly strain SB3086, deposit No. ATCC 55406, International Publication No. 2003 / 000051 (available from Novozymes as ECOGUARD® biopesticide and GREEN RELEAF™); (B1.12) Paenibacillus sp. strain deposit No. NRRL B-50972 or deposit No. NRRL B-67129, International Publication No. 2016 / 154297; (B1.13) Bacillus subtilis strain BU1814 (available from BASF SE as VELONDIS® PLUS, VELONDIS® FLEX and VELONDIS® EXTRA); (B1.14) Bacillus subtilis CX-9060 from Certis USA LLC, a Mitsui & Co. subsidiary; (B1.15) Bacillus amyloliquefaciens strain F727 (also known as strain MBI110) (NRRL deposit No. B-50768; International Publication No. 2014 / 028521) (available from Marrone Bio Innovations as STARGUS®); (B1.16) Bacillus amyloliquefaciens strain FZB42, deposit No. DSM 23117 (available from ABiTEP, Germany, as RHIZOVITAL®); (B1.17) From Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (FMC Corporation as QUARTZO® (WG) and PRESENCE® (WP)); (B1.18) Bacillus mojavensis strain R3B (Deposit No. NCAIM(P)B001389) (International Publication No. 2013 / . From Certis USA LLC, a subsidiary of Mitsui & Co. (034938); (B1.19) Paenibacillus polymyxa ssp. Plantarum (International Publication No. WO 2016 / 020371), from BASF SE; (B1.20) Paenibacillus epiphyticus (International Publication No. WO 2016 / 020371), from BASF SE; (B1.21) Pseudomonas chlororaphis strain AFS009, Deposit No. NRRL B-50897, International Publication No. WO 2017 / 019448 (e.g., from AgBiome Innovations, USA, as HOWLER™ and ZIO®); (B1.22) Pseudomonas chlororaphis, particularly strain MA342 (e.g., from Bioagri and Koppert, as CEDOMON®, CERALL®, and CEDRESS®); (B1.23) Streptomyces lydicus strain WYEC108 (also known as Streptomyces lydicus strain WYCD108US) (from Novozymes, as ACTINO-IRON® and ACTINOVATE®); (B1.24) Agrobacterium radiobacter strain K84 (e.g., from AgBioChem, Canada, as GALLTROL-A®); (B1.25) Agrobacterium radiobacter strain K1026 (e.g., from BASF SE, as NOGALL™); (B1.26) Bacillus subtilis KTSB strain (from Donaghys, as FOLIACTIVE®); (B1.27) Bacillus subtilis IAB / BS03 (from STK Bio-Ag Technologies, as AVIV™); (B1.28) Bacillus subtilis strain Y1336 (available from Bion-Tech, Taiwan, as BIOBAC® WP, registered in Taiwan under registration numbers 4764, 5454, 5096 and 5277 as a biocide fungicide); (B1.29) Bacillus amyloliquefaciens isolate B246 (e.g., from Pretoria University as AVOGREEN™); (B1.30) Bacillus methylotrophicus strain BAC-9912 (from Shenyang Institute of Applied Ecology); (B1.31) Pseudomonas proradix (e.g., from Sourcon Padena as PRORADIX®); (B1.32) Streptomyces griseoviridis strain K61 (also known as Streptomyces galbus strain K61) (Deposit No. DSM 7206) (from Verdera as MYCOSTOP®; from BioWorks as PREFENCE®; see Crop Protection 2006, 25, 468 - 475); (B1.33) Pseudomonas fluorescens strain A506 (e.g., from NuFarm as BLIGHTBAN® A506); and (B2) Fungi, such as: (B2.01) *Coniothyrium minitans*, in particular, strain CON / M / 91-8 (Deposit No. DSM-9660; for example, from Bayer CropScience Biologics GmbH as Contans®); (B2.02) *Metschnikowia fructicola*, in particular, strain NRRL Y-30752; (B2.03) *Microsphaeropsis ochracea*; (B2.04) *Trichoderma atroviride*, in particular, strain SC1 (Deposit No. CBS 122089, International Publication No. WO 2009 / 116106 and US Patent No. 8,431,120 (from Bi-PA)), strain 77B (as T77 from Andermatt Biocontrol) or strain LU132 (for example, from Agrimm Technologies Limited as Sentinel); (B2.05) *Trichoderma harzianum* strain T-22 (for example, from Andermatt Biocontrol or Koppert as Trianum-P) or strain Cepa Simb-T5 (from Simbiose Agro); (B2.06) *Gliocladium roseum* (also known as *Clonostachys rosea* f. *rosea*), in particular, strain 321U from Adjuvants Plus, strain ACM941 disclosed by Xue (Efficacy of Clonostachys rosea strain ACM941 and fungicide seed treatments for controlling the root rot complex of field pea, Can Jour Plant Sci 83(3): 519-524), or strain IK726 (Jensen DF, et al.Development of a biocontrol agent for plant disease control with special emphasis on the near commercial fungal antagonist Clonostachys rosea strain ‘IK726’; Australas Plant Pathol. 2007;36:95-101); (B2.07) Talaromyces flavus, strain V117b; (B2.08) Trichoderma viride, in particular, strain B35 (Pietr et al., 1993, Zesz. Nauk. A R w Szczecinie 161: 125-137); (B2.09) Trichoderma asperellum, in particular, strain SKT-1, deposit No. FERM P-16510 (for example, from Kumiai Chemical Industry as ECO-HOPE®), strain T34 (for example, from Biocontrol Technologies S.L., Spain as T34 Biocontrol) or strain ICC 012 from Isagro; (B2.10) Trichoderma atroviride, strain CNCM I-1237 (for example, from Agrauxine, France as Esquive® WP); (B2.11) Trichoderma atroviride, strain No. V08 / 002387; (B2.12) Trichoderma atroviride, strain NMI No. V08 / 002388; (B2.13) Trichoderma atroviride... Trichoderma atroviride, strain NMI No. V08 / 002389; (B2.14) Trichoderma atroviride, strain NMI No. V08 / 002390; (B2.15) Trichoderma atroviride, strain LC52 (for example, from Agrimm Technologies Limited as Tenet); (B2.16) Trichoderma atroviride, strain ATCC 20476 (IMI 206040); (B2.17) Trichoderma atroviride, strain T11 (IMI352941 / CECT20498); (B2.18) Trichoderma harmatum; (B2.19) Trichoderma harzianum; (B2.20) Trichoderma harzianum rifai T39 (for example, from Makhteshim, USA as Trichodex®); (B2.21) Trichoderma asperellum, particularly strain kd (for example, from Andermatt Biocontrol as T-Gro); (B2.22) Trichoderma harzianum strain ITEM 908 (for example, from Koppert as Trianum-P); (B2.23) Trichoderma harzianum strain TH35 (for example, from Mycontrol as Root-Pro); (B2.24) Trichoderma virens (also known as Gliocladium virens), particularly strain GL-21 (for example, from Certis, USA as SoilGard); (B2.25) Trichoderma viride, strain TV1 (for example, from Koppert as Trianum-P); (B2.26) Ampelomyces quisqualis, in particular strain AQ 10 (e.g., from IntrachemBio Italia as AQ 10®); (B2.27) Aureobasidium pullulans, in particular the budding spores of strain DSM14940; (B2.28) Aureobasidium pullulans,. In particular, the endospores of DSM 14941; (B2.29) Aureobasidium pullulans, in particular, the mixture of endospores of DSM 14940 and DSM 14941 (for example, from bio-ferm as Botector® from Switzerland); (B2.30) Cladosporium cladosporioides, strain H39, deposit No. CBS 122244, US Patent Application Publication No. 2010 / 0291039 (Stichting Dienst Landbouwkundig Onderzoek); (B2.31) Gliocladium catenulatum (synonym: Clonostachys rosea f. catenulate) strain J1446 (for example, from Lallemand as Prestop®); (B2.32) the conidia of Lecanicillium lecanii (formerly known as Verticillium lecanii) strain KV01 (for example, from Koppert / Arysta as Vertalec®); (B2.33) Penicillium vermiculatum; (B2.34) Pichia anomala, strain WRL-076 (NRRL Y-30842), US Patent No. 7,579,183; (B2.35) Trichoderma atroviride, strain SKT-1 (FERM P-16510), JP-A-11-253151; (B2.36) Trichoderma atroviride, strain SKT-2 (FERM P-16511), JP-A-11-253151; (B2.37) Trichoderma atroviride, strain SKT-3 (FERM P-17021), JP-A-11-253151; (B2.38) Trichoderma gamsii (former name T. viride (T.viride)), strain ICC080 (IMI CC 392151 CABI, for example, as BioDerma from AGROBIOSOL DE MEXICO, S.A.DE C.V.); (B2.39) Trichoderma harzianum strain DB 103 (available from Dagutat Biolab as T-GRO® 7456); (B2.40) Trichoderma polysporum, strain IMI 206039 (for example, as Binab TF WP from BINAB Bio-Innovation AB, Sweden); (B2.41) Trichoderma stromaticum, deposit No. Ts3550 (for example, as Tricovab from CEPLAC, Brazil). (B2.42) Ulocladium oudemansii strain U3, deposit No. NM99 / 06216 (e.g., from Botry-Zen Ltd, New Zealand as BOTRY-ZEN® and from BioWorks, Inc. as BOTRYSTOP®); (B2.43) Verticillium albo-atrum (synonym V. dahliae), strain WCS850, deposit No. WCS850, deposited with the Central Bureau for Fungi Cultures (e.g., from Tree Care Innovations as DUTCH TRIG®); (B2.44) Verticillium chlamydosporium; (B2.45) A mixture of Trichoderma asperellum strain ICC 012 (also known as Trichoderma harzianum ICC012), deposit No. CABI CC IMI 392716 and Trichoderma gamsii (synonym T. viride) strain ICC 080, deposit No. IMI 392151 (e.g., from Isagro USA, Inc. as BIO-TAM™ and from Agrobiosol de Mexico as BIODERMA®), from S.A. de C.V.); (B2.46) Trichoderma asperelloides JM41R (deposit No. NRRL B-50759) (from BASF SE as TRICHO PLUS®); (B2.47) Aspergillus flavus strain NRRL 21882 (product known as AFLA-GUARD® from Syngenta / ChemChina); (B2.48) Chaetomium cupreum (deposit No. CABI 353812) (e.g., from AgriLife as BIOKUPRUM™); (B2.49) Saccharomyces cerevisiae, in particular, strain LASO2 (from Agro-Levures et Derives), strain LAS117 cell wall (from Lesaffre as CEREVISANE®; from BASF SE as ROMEO®), strains CNCM No. I-3936, CNCM No. I-3937, CNCM No. I-3938, CNCM No. I-3939 (from Lesaffre et Compagnie, France as International Publication No. 2010 / 086790); (B2.50) Trichoderma virens strain G-41, formerly known as Gliocladium virens (deposit No. ATCC 20906) (e.g., from BioWorks, USA as ROOTSHIELD® PLUS WP and TURFSHIELD® PLUS WP); (B2.51) Trichoderma hamatum, deposit No. ATCC 28012; (B2.52) Ampelomyces quisqualis strain AQ10, deposit No. CNCM I-807 (e.g., from IntrachemBio Italia as AQ 10®); (B2.53) Phlebiopsis gigantea strain VRA 1992 (from Danstar Ferment as ROTSTOP® C); (B2.54) Penicillium steckii (DSM 27859; International Publication No. WO 2015 / 067800) from BASF SE; (B2.55) Chaetomium globosum (available from Rivale as RIVADIOM®); (B2.56) Cryptococcus flavescens, strain 3C (NRRL Y-50378); (B2.57) Dactylaria candida; (B2.58) Dilophosphora alopecuri (available as TWIST FUNGUS®); (B2.59) Fusarium oxysporum, strain Fo47 (available from Natural Plant Protection as FUSACLEAN®); (B2.60) Pseudozyma flocculosa, strain PF-A22 UL (available from Plant Products Co., Canada as SPORODEX® L); (B2.61) Trichoderma gamsii (formerly 'T. viride'), strain ICC 080 (IMI CC 392151 CABI) (available from AGROBIOSOL DE MEXICO, S.A.DE C.V. as BIODERMA®); (B2.62) Trichoderma fertile (e.g., from BASF as the product TrichoPlus); (B2.63) Muscodor roseus, particularly strain A3-5 (Deposit No. NRRL 30548); (B2.64) Simplicillium lanosoniveum; Strain 3C (NRRL Y-50378); (B2.57) Dactylaria candida; (B2.58) Dilophosphora alopecuri (available as TWIST FUNGUS®); (B2.59) Fusarium oxysporum, strain Fo47 (available from Natural Plant Protection as FUSACLEAN®); (B2.60) Pseudozyma flocculosa, strain PF-A22 UL (available from Plant Products Co., Canada as SPORODEX® L); (B2.61) Trichoderma gamsii (formerly 'T. viride'), strain ICC 080 (IMI CC 392151 CABI) (available from AGROBIOSOL DE MEXICO, S.A.DE C.V. as BIODERMA®); (B2.62) Trichoderma fertile (e.g., from BASF as the product TrichoPlus); (B2.63) Muscodor roseus, particularly strain A3-5 (Deposit No. NRRL 30548); (B2.64) Simplicillium lanosoniveum; (C) A biocontrol agent having the effect of improving plant growth and / or plant health, which may be combined with a compound combination according to the present invention and comprising the following: (C1) Bacteria selected from the group consisting of the following: (C1.01) Bacillus pumilus (Bacillus pumilus), in particular, strain QST2808 (Deposit No. NRRL No. B-30087); (C1.02) Bacillus subtilis, in particular, strain QST713 / AQ713 (deposited with NRRL under No. B-21661 and described in U.S. Patent No. 6,060,051; available from Bayer CropScience LP, USA as SERENADE® OPTI or SERENADE® ASO); (C1.03) Bacillus subtilis, in particular, strain AQ30002 (described in Deposit No. NRRL B-50421 and U.S. Patent Application Publication No. 13 / 330,576); (C1.04) Bacillus subtilis, in particular, strain AQ30004 (and described in NRRL B-50455 and U.S. Patent Application Publication No. 13 / 330,576); (C1.05) Sinorhizobium meliloti strain NRG-185-1 (from Bayer CropScience as NITRAGIN® GOLD); (C1.06) Bacillus subtilis strain BU1814, (available from BASF SE as TEQUALIS®); (C1.07) Bacillus subtilis rm303 (from Biofilm Crop Protection as RHIZOMAX®); (C1.08) Bacillus amyloliquefaciens pm414 (from Biofilm Crop Protection as LOLI-PEPTA®); (C1.09) Bacillus mycoides BT155 (NRRL No. B-50921), (C1.10) Bacillus mycoides EE118 (NRRL No. B-50918), (C1.11) Bacillus mycoides EE141 (NRRL No. B-50916), (C1.12) Bacillus mycoides BT46-3 (NRRL No. B-50922), (C1.13) Bacillus cereus family member EE128 (NRRL No. B-50917), (C1.14) Bacillus thuringiensis BT013A (NRRL No. B-50924), also known as Bacillus thuringiensis 4Q7, (C1.15) Bacillus cereus family member EE349 (NRRL No. B-50928), (C1.16) Bacillus amyloliquefaciens SB3281 (ATCC# PTA-7542; International Publication No. WO 2017 / 205258), (C1.17) Bacillus amyloliquefaciens TJ1000 (available from Novozymes as QUIKROOTS®); (C1.18) Bacillus firmus, in particular, strain CNMC I-1582 (e.g., from BASF SE as VOTIVO®); (C1.19) Bacillus pumilus, in particular, strain GB34 (e.g., from Bayer Crop Science, Germany as YIELD SHIELD®); (C1.20) Bacillus amyloliquefaciens, in particular, strain IN937a; (C1.21) Bacillus amyloliquefaciens, in particular, strain FZB42 (e.g., from ABiTEP, Germany as RHIZOVITAL®); (C1.22) Bacillus amyloliquefaciens BS27 (Deposit No. NRRL B-5015); (C1.23) A mixture of Bacillus licheniformis FMCH001 and Bacillus subtilis FMCH002 (available from FMC Corporation as QUARTZO® (WG), PRESENCE® (WP)); (C1.24) Bacillus cereus, particularly strain BP01 (ATCC 55675; e.g., from Arysta Lifescience as MEPICHLOR®, from the United States); (C1.25) Bacillus subtilis, particularly strain MBI 600 (e.g., from BASF SE as SUBTILEX®); (C1.26) Bradyrhizobium japonicum (e.g., from Novozymes as OPTIMIZE®); (C1.27) Mesorhizobium cicer (e.g., from BASF SE as NODULATOR); (C1.28) Rhizobium leguminosarium biovar viciae (e.g., from BASF SE as NODULATOR); (C1.29) Delftia acidovorans, particularly strain RAY209 (e.g., from Brett Young Seeds as BIOBOOST®); (C1.30) Lactobacillus sp. (e.g., from LactoPAFI as LACTOPLANT®); (C1.31) Paenibacillus polymyxa, particularly strain AC-1 (e.g., from Green Biotech Company Ltd. as TOPSEED®); (C1.32) Pseudomonas proradix (e.g., from Sourcon Padena as PRORADIX®); from the United States); (C1.25) Bacillus subtilis, particularly strain MBI 600 (e.g., from BASF SE as SUBTILEX®); (C1.26) Bradyrhizobium japonicum (e.g., from Novozymes as OPTIMIZE®); (C1.27) Mesorhizobium cicer (e.g., from BASF SE as NODULATOR); (C1.28) Rhizobium leguminosarium biovar viciae (e.g., from BASF SE as NODULATOR); (C1.29) Delftia acidovorans, particularly strain RAY209 (e.g., from Brett Young Seeds as BIOBOOST®); (C1.30) Lactobacillus sp. (e.g., from LactoPAFI as LACTOPLANT®); (C1.31) Paenibacillus polymyxa, particularly strain AC-1 (e.g., from Green Biotech Company Ltd. as TOPSEED®); (C1.32) Pseudomonas proradix (e.g., from Sourcon Padena as PRORADIX®); (C1.33) *Azospirillum brasilense* (e.g., from KALO, Inc. as VIGOR®); (C1.34) *Azospirillum lipoferum* (e.g., from TerraMax, Inc. as VERTEX-IF™); (C1.35) A mixture of *Azotobacter vinelandii* and *Clostridium pasteurianum* (available from Agrinos as INVIGORATE®); (C1.36) *Pseudomonas aeruginosa*, particularly, strain PN1; (C1.37) *Rhizobium leguminosarum*, particularly, biovar viceae strain Z25 (Deposit No. CECT 4585); (C1.38) *Azorhizobium caulinodans*, particularly, strain ZB-SK-5; (C1.39) *Azotobacter chroococcum*, particularly, strain H23; (C1.40) *Azotobacter vinelandii*, particularly, strain ATCC 12837; (C1.41) *Bacillus siamensis*, particularly, strain KCTC 13613T; (C1.42) *Bacillus tequilensis*, particularly, strain NII-0943; (C1.43) *Serratia marcescens*, particularly, strain SRM (Deposit No. MTCC 8708); (C1.44) *Thiobacillus sp.* (e.g., from Cropaid Ltd UK as CROPAID®); and (C2) Fungi selected from the group consisting of: (C2.01) Purpureocillium lilacinum (formerly known as Paecilomyces lilacinus), strain 251 (AGAL 89 / 030550; from Bayer CropScience Biologics GmbH, for example, as BioAct); (C2.02) Penicillium bilaii, strain ATCC 22348 (from Acceleron BioAg, for example, as JumpStart®); (C2.03) Talaromyces flavus, strain V117b; (C2.04) Trichoderma atroviride, strain CNCM I-1237 (from Agrauxine, France, for example, as Esquive® WP); (C2.05) Trichoderma viride, for example, strain B35 (Pietr et al., 1993, Zesz. Nauk. A R w Szczecinie 161: 125-137); (C2.06) Trichoderma atroviride, strain LC52 (also known as Trichoderma atroviride strain LU132; from Agrimm Technologies Limited, for example, as Sentinel); (C2.07) Trichoderma atroviride, strain SC1, described in International Application No. PCT / IT2008 / 000196); (C2.08) Trichoderma asperellum, strain kd (from Andermatt Biocontrol, for example, as T-Gro); (C2.09) Trichoderma asperellum, strain Eco-T (Plant Health Products, South Africa); (C2.10) Trichoderma harzianum strain T-22 (e.g., from Andermatt Biocontrol or Koppert as Trianum-P); (C2.11) Myrothecium verrucaria strain AARC-0255 (e.g., from Valent Biosciences as DiTera™); (C2.12) Penicillium bilaii strain ATCC ATCC20851; (C2.13) Pythium oligandrum strain M1 (ATCC 38472; e.g., from Bioprepraty, Czech Republic as Polyversum); (C2.14) Trichoderma virens strain GL-21 (e.g., from Certis, USA as SoilGard®); (C2.15) Verticillium albo-atrum (formerly V. dahliae) strain WCS850 (CBS 276.92; e.g., from Tree Care Innovations as Dutch Trig); (C2.16) Trichoderma atroviride, in particular, strain No. V08 / 002387, strain No. NMI No. V08 / 002388, strain No. NMI No. V08 / 002389, strain No. NMI No. V08 / 002390; (C2.17) Trichoderma harzianum strain ITEM 908; (C2.18) Trichoderma harzianum, strain TSTh20; (C2.19) Trichoderma harzianum strain 1295-22; (C2.20) Pythium oligandrum strain DV74; (C2.21) Rhizopogon amylopogon (e.g., included in Myco-Sol from Helena Chemical Company); (C2.(22) Rhizopogon fulvigleba (for example, contained in Myco-Sol from Helena Chemical Company); and (C2.23) Trichoderma virens strain GI-3;. (D) An insecticidal active biocontrol agent selected from the following: (D1) Bacteria selected from the group consisting of the following: (D1.01) Bacillus thuringiensis subsp. aizawai, in particular, strain ABTS-1857 (SD-1372; for example, from Valent BioSciences as XENTARI®); (D1.02) Bacillus mycoides isolate J. (for example, from Certis USA LLC, a Mitsui & Co. subsidiary as BmJ); (D1.03) Bacillus sphaericus, in particular, serotype H5a5b strain 2362 (strain ABTS-1743) (for example, from Valent BioSciences, USA as VECTOLEX®); (D1.04) Bacillus thuringiensis subsp. kurstaki strain BMP 123 from Becker Microbial Products, State of Israel; (D1.05) Bacillus thuringiensis subsp. aizawai, in particular, serotype H-7 (for example, from Valent BioSciences, USA as FLORBAC® WG); (D1.06) Bacillus thuringiensis subsp. kurstaki strain HD-1 (for example, DIPEL (registered trademark) ES from Valent BioSciences, USA; (D1.07) Bacillus thuringiensis subsp. kurstaki strain BMP 123 from Becker Microbial Products, Israel; (D1.08) Bacillus thuringiensis israelensis strain BMP 144 (e.g., as AQUABAC (registered trademark) from Becker Microbial Products, Israel); (D1.09) Burkholderia spp., particularly Burkholderia rinojensis strain A396 (also known as Burkholderia rinojensis strain MBI 305) (Deposit No. NRRL B-50319; International Publication Nos. WO 2011 / 106491 and WO 2013 / 032693; e.g., as MBI-206 TGAI and ZELTO (registered trademark) from Marrone Bio Innovations); (D1.10) Chromobacterium subtsugae, particularly strain PRAA4-1T (MBI-203; e.g., as GRANDEVO (registered trademark) from Marrone Bio Innovations); (D1.11) Paenibacillus popilliae (formerly Bacillus popilliae); e.g., as MILKY SPORE POWDER (trademark) and MILKY SPORE GRANULAR (trademark) from St. Gabriel Laboratories); (D1.12) Bacillus thuringiensis subsp. israelensis (serotype H-14) strain AM65-52 (Deposit No. ATCC 1276) (e.g., as VECTOBAC (registered trademark) from Valent BioSciences, USA); (D1.13) Bacillus thuringiensis var. kurstaki strain EVB-113-19 (e.g., from AEF Global as BIOPROTEC®); (D1.14) Bacillus thuringiensis subsp. tenebrionis strain NB 176 (SD-5428; e.g., from BioFa Germany as NOVODOR® FC); (D1.15) Bacillus thuringiensis var. japonensis strain Buibui; (D1.16) Bacillus thuringiensis subsp. kurstaki strain ABTS 351; (D1.17) Bacillus thuringiensis subsp. kurstaki strain PB 54; (D1.18) Bacillus thuringiensis subsp. kurstaki strain SA 11; (D1.19) Bacillus thuringiensis subsp. kurstaki strain SA 12; (D1.20) Bacillus thuringiensis subsp. kurstaki strain EG 2348; (D1.21) Bacillus thuringiensis var. Colmeri (e.g., from Changzhou Jianghai Chemical Factory as TIANBAOBTC); (D1.22) Bacillus thuringiensis subsp. aizawai strain GC-91; (D1.23) Serratia entomophila (e.g., from Wrightson Seeds as INVADE®); (D1.24) Serratia marcescens, particularly strain SRM (Deposit No. MTCC 8708); and (D1.25) Wolbachia pipientis strain ZAP (e.g., from MosquitoMate as ZAP MALES®); and... (D2)(D2.01) Isaria fumosorosea (formerly known as Paecilomyces fumosoroseus) strain apopka 97; (D2.02) Beauveria bassiana strain ATCC 74040 (e.g., from Intrachem Bio Italia as NATURALIS®); (D2.03) Beauveria bassiana strain GHA (Deposit No. ATCC74250; e.g., from Laverlam International Corporation as BOTANIGUARD® ES and MYCONTROL - O®); (D2.04) Zoophtora radicans; (D2.05) Metarhizium robertsii 15013 - 1 (deposited at NRRL Deposit No. 67073), (D2.06) Metarhizium robertsii 23013 - 3 (deposited at NRRL Deposit No. 67075), and (D2.07) Metarhizium anisopliae 3213 - 1 (deposited at NRRL Deposit No. 67074) (International Publication No. WO 2017 / 066094; Pioneer Hi - Bred International); (D2.08) a fungus selected from the group consisting of Beauveria bassiana strain ATP02 (Deposit No. DSM 24665); (E) A virus selected from the group consisting of Adoxophyes orana (apple tortrix) granulosis virus (GV), Cydia pomonella (codling moth) granulosis virus (GV), Helicoverpa armigera (American tobacco budworm larva) nuclear polyhedrosis virus (NPV), Spodoptera exigua (beet armyworm larva) mNPV, Spodoptera frugiperda (fall armyworm) mNPV, and Spodoptera littoralis (African cotton leafworm) NPV; (F) Bacteria and fungi that can be added as "inoculum" to plants or plant parts or plant organs and that, due to their specific properties, promote plant growth and plant health. For example: Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., in particular Burkholderia cepacia (formerly known as Pseudomonas cepacia), Gigaspora spp., or Gigaspora monosporum, Glomus spp., Laccaria spp., Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., in particular Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suillus spp., and Streptomyces spp.; and (G) Allium sativum, Artemisia absinthium, azadirachtin, Bio-Keeper WP, Cassia nigricans, Celastrus angulatus, Chenopodium anthelminticum, chitin, Armour-Zen, Dryopteris filix-mas, Equisetum arvense, Fortune Aza, Fungastop, Heads Up (Chenopodium quinoa saponin extract), pyrethrum / pyrethrins, Quassia amara, Quercus, Quillaja, Regalia, "Requiem (trademark) insecticide", rotenone, ryania / ryanodine, Symphytum officinale, Tanacetum vulgare, thymol, Triact 70, TriCon, Tropaeulum majus, Urtica dioica, veratrin, Viscum album, Brassicaceae extract, in particular, rapeseed powder or mustard powder, and as an active ingredient, for example, olive oil contained in a product with the trade name FLiPPER (registered trademark), in particular, an unsaturated fatty acid / carboxylic acid having a carbon chain length C 16 ~C 20 Plant extracts and products produced by microorganisms containing proteins and secondary metabolites that can be used as biological control agents such as biopesticide / acaricide active substances obtained from unsaturated fatty acids / carboxylic acids having

[0119] The compounds and compositions of the present invention may be combined with one or more active ingredients selected from insecticides, acaricides, and nematicides.

[0120] The term "insecticide" and the term "insecticidal" refer to the ability of a substance to increase the mortality rate of insects or inhibit their growth rate. As used herein, the term "insect" includes all organisms of the class "Insecta".

[0121] The term "nematicide" and "nematicidal" refer to the ability of a substance to increase the mortality rate of nematodes or inhibit their growth rate. Generally, "nematodes" include the eggs, larvae, juveniles, and mature forms of said organisms.

[0122] The term "acaricide" and "acaricidal" refer to the ability of a substance to increase the mortality rate or inhibit the growth rate of ectoparasites belonging to the subclass Acari of the class Arachnida.

[0123] Examples of insecticides, acaricides, and nematicides that can be mixed with the compounds and compositions of the present invention are as follows (1) to (33), respectively: (1) An acetylcholinesterase (AChE) inhibitor, preferably a carbamate selected from aldicarb, aldicarb sulfoxide, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC, and xylylcarb, or an organophosphate selected from acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorate, chlorfenvinphos, chlormephos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos / DDVP, dichlorvos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, etoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O-(methoxyaminothiophosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thimet, triazophos, trichlorfon, and vamidothion.

[0124] (2) A GABAergic chloride ion channel blocker, preferably a cyclodiene-organochlorine selected from chlordane and endosulfan, or a phenylpyrazole (fiproles) selected from ethiprole and fipronil.

[0125] (3) Sodium channel modifying factors, preferably pyrethroids selected from acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin s-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, β-cyhalothrin, cyhalothrin, λ-cyhalothrin, γ-cyhalothrin, cypermethrin, α-cypermethrin, β-cypermethrin, θ-cypermethrin, ζ-cypermethrin, cyphenothrin [(1R)-trans isomer], deltamethrin, empenthrin [(EZ)-(1R) isomer], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, momfluorothrin, permethrin, phenothrin [(1R)-trans isomer], prallethrin, pyrethrin (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)-isomer)], tralomethrin and transfluthrin or DDT or methoxychlor.

[0126] (4) Nicotinic acetylcholine receptor (nAChR) competitive modulators, preferably neonicotinoids selected from acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam, or nicotine, or sulfoximines selected from sulfoxaflor, or butenolides selected from flupyradifurone, or mesoionic compounds selected from triflumizopyrim.

[0127] (5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators (site I), preferably spinosins selected from spinetoram and spinosad.

[0128] (6) Glutamate-gated chloride ion channel (GluCl) allosteric modulators, preferably abamectin, emamectin benzoate, lepimectin, and milbemectin, which are selected from the avermectin / milbemycin group.

[0129] (7) Juvenile hormone mimics, preferably hydroprene, kinoprene, and methoprene, or juvenile hormone analogs selected from fenoxycarb or pyriproxyfen.

[0130] (8) Various non-specific (multisite) inhibitors, preferably alkyl halides selected from methyl bromide and other halogenated alkyls; or methyl isocyanate generators selected from chloropicrin, sulfuryl fluoride, borax, tartar emetic, dazomet, and metam.

[0131] (9) Chordotonal organ TRPV channel modulators, preferably pyridine azomethanes selected from pimetrozine and pyrifluquinazone, or pyropenes selected from afidopyropen.

[0132] (10) Acarid growth inhibitors that act on CHS1, selected from clofentezine, hexythiazox, diflovidazin, and etoxazole.

[0133] (11) A microbial disruptor of the insect midgut selected from Bacillus thuringiensis subsp. israelensis, Bacillus sphaericus, Bacillus thuringiensis subsp. aizawai, Bacillus thuringiensis subsp. kurstaki, Bacillus thuringiensis subsp. tenebrionis, and a B.t. plant protein selected from Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, and Cry34Ab1 / 35Ab1.

[0134] (12) An inhibitor of mitochondrial ATP synthase, preferably an ATP disruptor selected from diafenthiuron, or an organotin compound selected from azocyclotin, cyhexatin, and fenbutatin oxide, or propargite or tetradifon.

[0135] (13) An uncoupler of oxidative phosphorylation by disruption of the proton gradient selected from chlorfenapyr, DNOC, and sulfiramid.

[0136] (14) A nicotinic acetylcholine receptor channel blocker selected from bensultap, cartap hydrochloride, thiosiram, and sodium thiosultap.

[0137] (15) An inhibitor of chitin biosynthesis acting on CHS1, preferably a benzoylurea selected from bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, and triflumuron.

[0138] (16) An inhibitor of chitin biosynthesis selected from buprofezin, type 1.

[0139] (17) A molting disruptor selected from silafluofen (especially for Diptera, i.e., Diptera).

[0140] (18) Preferably, an ecdysone receptor agonist selected from chromafenozide, halofenozide, methoxyfenozide, and tebufenozide.

[0141] (19) An octopamine receptor agonist selected from amitraz.

[0142] (20) A mitochondrial electron transport system complex III inhibitor selected from hydramethylnon, acequinocyl, fluacrypyrim, and bifenazate.

[0143] (21) A mitochondrial electron transport system complex I inhibitor, preferably a METI acaricide and insecticide selected from phenazakine, fenpyroximate, pyrimidifen, pydaben, tebufenpyrad, and tolfenpyrad, or rotenone (derris).

[0144] (22) A voltage-dependent sodium channel inhibitor, preferably oxadiazines selected from indoxacarb, or semicarbazones selected from metaflumizone.

[0145] (23) An inhibitor of acetyl-CoA carboxylase, preferably tetronic acid and tetramic acid derivatives selected from spirodiclofen, spirotetramat, spirodiclofen, and spirotetramat.

[0146] (24) A mitochondrial electron transport system complex IV inhibitor, preferably phosphines selected from aluminum phosphide, calcium phosphide, phosphine hydride, and zinc phosphide, or cyanides selected from calcium cyanide, potassium cyanide, and sodium cyanide.

[0147] (25) Mitochondrial electron transport chain complex II inhibitor, preferably a β-ketonitrile derivative selected from cyenopyrafen and siflumetofen, or carboxanilides selected from piflubumide.

[0148] (28) Ryanodine receptor modulator, preferably diamides selected from chlorantraniliprole, cyantraniliprole, flubendiamide and tetraniliprole.

[0149] (29) Chordotonal organ modulator (with an unclear target site) selected from flonicamid.

[0150] (30) GABAergic chloride ion channel allosteric modulator, preferably meta-diamides selected from broflanilide, or isoxazoles selected from fluxametamide.

[0151] (31) Baculovirus, preferably granulovirus (GV) selected from Cydia pomonella GV and Thaumatotibia leucotreta (GV), or nucleopolyhedrovirus NPV selected from Anticarsia gemmatalis MNPV, flubendiamide and Helicoverpa armigera NPV.

[0152] (32) Nicotinic acetylcholine receptor allosteric modulator (site II) selected from GS-ω / κHXTX-Hv1a peptide.

[0153] (33) Further active compounds selected from the following: Acequinocyl, afoxolaner, azadirachtin, benclothiaz, benzoximate, benzpyrimoxan, bromopropylate, chinomethionat, chloroprallethrin, cryolite, cyclobutrifluram, cycloxaprid, cyetpyrafen, cyhalodiamide, cyproflanilide (CAS 2375110-88-4), dichloromethothiaz, dicofol, dinapropylate, e-methoftytrin, e-momfluorothrin, flometokine, fluaazindoline, flupyrimin, fluphenoxystrobin, flupyropene, flufenzin, flufenoxuron, flupyradifurone, fluopyram, flupyrimin, fluralaner, flufenoxuron, flupenthiopheneox, guazatine, heptafluthrin, imidaclothiz, iprodione, isocycloseram, k-bifenthrin, k-tefluthrin, lotilaner, meperfluthrin, nifupropyrone (CAS 1771741-86-6), oxathiapiprolin, pyriproxyfen, pyridalyl, pyrifluquinazon, pyriminostrobin, sarolaner, SpidoSmart, spirodiclofen, tetramethylfluthrin, tetrachlorantraniliprole, thiacloprid, thioxazafen, thiofluoximate, chlorantraniliprole, iodomethane; further active compounds selected from further formulations based on Bacillus firmus (I-1582, Votivo) and azadirachtin (BioNeem), and further the following compounds: 1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazol-5-amine (known from WO 2006 / 043635) (CAS 885026-50-6), 2-chloro-N-[2-{1-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]piperidin-4-yl}-4-(trifluoromethyl)phenyl]isonicotinamide (known from WO 2006 / 003494) (CAS 872999-66-1), 3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]decan-3-en-2-one (known from WO 2010 / 052161) (CAS 1225292-17-0), ethyl 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4.5]decan-3-en-4-yl carbonate (known from EP 2647626 A1) (CAS 1440516-42-6), PF1364 (known from JP 2010-018586) (CAS 1204776-60-2), (3E)-3-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-1,1,1-trifluoro-propan-2-one (known from WO 2013 / 144213) (CAS 1461743-15-6), N-[3-(benzylcarbamoyl)-4-chlorophenyl]-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide (known from WO 2010 / 051926) (CAS 1226889-14-0), 5-Bromo-4-chloro-N-[4-chloro-2-methyl-6-(methylcarbamoyl)phenyl]-2-(3-chloro-2-pyridyl)pyrazole-3-carboxamide (known from Chinese Patent No. 103232431) (CAS 1449220-44-3), 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxide-3-thietanyl)-benzamide, 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(trans-1-oxide-3-thietanyl)-benzamide and 4-[(5S)-5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxide-3-thietanyl)benzamide (known from International Publication No. 2013 / 050317(A1)) (CAS1332628-83-7), N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propanamide, (+)-N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propanamide and (-)-N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propanamide (known from International Publication No. 2013 / 162715(A2), International Publication No. 2013 / 162716(A2), US Patent Application Publication No. 2014 / 0213448(A1)) (CAS 1477923-37-7), 5-[[(2E)-3-chloro-2-propen-1-yl]amino]-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile (known from Chinese Patent Application Publication No. 101337937) (CAS 1105672-77-2), 3-bromo-N-[4-chloro-2-methyl-6-[(methylamino)thiomethyl]phenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide, (Liudaibenjiaxuanan, known from Chinese Patent Application Publication No. 103109816) (CAS 1232543-85-9); N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide (known from International Publication No. 2012 / 034403(A1)) (CAS 1268277-22-0), N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide (known from International Publication No. 2011 / 085575(A1)) (CAS 1233882-22-8), 4-[3-[2,6-dichloro-4-[(3,3-dichloro-2-propen-1-yl)oxy]phenoxy]propoxy]-2-methoxy-6-(trifluoromethyl)-pyrimidine (known from Chinese Patent Application Publication No. 101337940) (CAS 1108184-52-6); (2E)-and 2(Z)-2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl], -Hydrazinecarboxamide (known from Chinese Patent Application Publication No. 101715774) (CAS 1232543-85-9); 3-(2,2-dichloroethenyl)-2,2-dimethyl-4-(1H-benzimidazol-2-yl)phenyl-cyclopropanecarboxylic acid ester (known from Chinese Patent Application Publication No. 103524422) (CAS 1542271-46-4); (4aS)-7-chloro-2,5-dihydro-2-[[(methoxycarbonyl)[4-[(trifluoromethyl)thio]phenyl]amino]carbonyl]-indeno[1,2-e][1,3,4]oxadiazine-4a(3H)-carboxylic acid methyl ester (known from Chinese Patent Application Publication No. 102391261) (CAS 1370358-69-2); 6-deoxy-3-O-ethyl-2,4-di-O-methyl-, 1-[N-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1H-1,2,4-triazol-3-yl]phenyl]carbamate]-α-L-mannopyranose (known from US Patent Application Publication No. 2014 / 0275503(A1)) (CAS 1181213-14-8); 8-(2-cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-aza-bicyclo[3.2.1]octane (CAS 1253850-56-4), (8-anti)-8-(2-cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-aza-bicyclo[3.2.1]octane (CAS 933798-27-7), (8-syn)-8-(2-cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-aza-bicyclo[3.2.1] Octane (known from WO 2007 / 040280 (A1), WO 2007 / 040282 (A1)) (CAS 934001-66-8), N-[4-(aminothioxomethyl)-2-methyl-6-[(methylamino)carbonyl]phenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide (known from Chinese Patent Application Publication No. 103265527) (CAS 1452877-50-7), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-1,8-diazaspiro[4.5]decan-2,4-dione (known from WO 2014 / 187846 (A1)) (CAS 1638765-58-8), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-2-oxo-1,8-diazaspiro[4.5]deca-3-en-4-yl-ethyl carbonate (known from WO 2010 / 066780 (A1), WO 2011 / 151146 (A1)) (CAS 1229023-00-0), N-[1-[(2,6-difluorophenyl]-1H-pyrazol-3-yl]-2-(trifluoromethyl)benzamide (known from WO 2014 / 053450 (A1)) (CAS 1594624-87-9), N-[(2,. 6-(Difluorophenyl)-2H-1,2,3-triazol-4-yl]-2-(trifluoromethyl)benzamide (known from International Publication No. WO 2014 / 053450 (A1)) (CAS 1594637-65-6), N-[1-(3,5-Difluoro-2-pyridinyl)-1H-pyrazol-3-yl]-2-(trifluoromethyl)benzamide (known from International Publication No. WO 2014 / 053450 (A1)) (CAS 1594626-19-3), (3R)-3-(2-Chloro-5-thiazolyl)-2,3-dihydro-8-methyl-5,7-dioxo-6-phenyl-5H-thiazolo[3,2-a]pyrimidinium inner salt (known from International Publication No. WO 2018 / 177970 (A1)) (CAS 2246757-58-2); 3-(2-Chloro-5-thiazolyl)-2,3-dihydro-8-methyl-5,7-dioxo-6-phenyl-5H-thiazolo[3,2-a]pyrimidinium inner salt (known from International Publication No. WO 2018 / 177970 (A1)) (CAS 2246757-56-0); N-[3-Chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-2-(methylsulfonyl)-propanamide (known from International Publication No. WO 2019 / 236274 (A1)) (CAS 2396747-83-2), N-[2-Bromo-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]-6-(trifluoromethyl)phenyl]-2-fluoro-3-[(4-fluorobenzoyl)amino]-benzamide (known from International Publication No. WO 2019 / 059412 (A1)) (CAS 1207977-87-4), 3-Bromo-1-(3-chloro-2-pyridinyl)-N-[4,6-dichloro-3-fluoro-2-[(methylamino)carbonyl]phenyl]-1H-pyrazole-5-carboxamide (flubendiamide; known from Chinese Patent Application Publication No. CN 110835330, Chinese Patent Application Publication No. CN 106977494) (CAS: 2129147-03-9).

[0154] Examples of nematicides that can be mixed with the compounds and compositions of the present invention are as follows: (Group N-1) Acetylcholinesterase (AChE) inhibitors, preferably carbamates selected from (N-1A) alanicarb, benfuracarb, carbofuran, carbosulfan, and thiodicarb, or (N-1B) cadusafos, ethoprophos, fenamiphos, fosthiazate, imicyafos, phorate, and terbufos, which are organophosphates.

[0155] (Group N-2) Glutamate-dependent chloride ion channel (GluCl) allosteric modulators, preferably avermectins selected from abamectin and emamectin benzoate.

[0156] (Group N-3) Mitochondrial electron transport system complex II inhibitors, particularly inhibitors of succinate coenzyme Q reductase, preferably pyridinylmethyl-benzamides selected from fluopyram.

[0157] (Group N-4) Lipid synthesis / growth regulation modulators, particularly inhibitors of acetyl-CoA carboxylase, preferably tetronic acid and tetramic acid derivatives selected from spirotetramat.

[0158] (Group N-UN) Compounds that act in an unknown or uncertain mode with various chemicals selected from fluensulfone, fluazaindoline, furfural, iprodione, and thioxazafen.

[0159] (Group N-UNX) Compounds with unknown or uncertain modes of action: putative multi-site inhibitors, preferably volatile sulfur-generating substances selected from carbon disulfide and dimethyl disulfide (DMDS), or carbon disulfide-releasing substances selected from sodium tetrathiocarbonate, or alkyl halides selected from methyl bromide and methyl iodide (iodomethane), or halogenated hydrocarbons selected from 1,2-dibromo-3-chloropropane (DBCP) and 1,3-dichloropropene, or methyl isothiocyanate-generating substances selected from allyl isothiocyanate, diazomethane, metam potassium, and metam sodium.

[0160] (Group N-UNB) Bacterial agents (non-Bt) with unknown or uncertain modes of action, preferably from the genus Burkholderia, such as rinojensis A396, the genus Bacillus, such as firmus, licheniformis, amyloliquefaciens or subtilis, the genus Pasteuria, such as penetrans or nishizawae, the genus Pseudomonas, such as chlororaphis or fluorescens, and the genus Streptomyces, such as lydicus, dicklowii or albogriseolus, or bacteria-derived.

[0161] (Group N-UNF) A fungicide with an unknown or uncertain mode of action, preferably a fungus or fungus-derived one selected from Actinomyces spp., such as Streptococcus, Arthrobotrys spp., such as oligospora, Aspergillus spp., such as niger, Muscodor spp., such as albus, Myrothecium spp., such as verrucaria, Paecilomyces spp., such as lilacinus (Purpureocillium lilacinum), carneus or fumosoroseus, Pochonia spp., such as chlamydosporia, and Trichoderma spp., such as harzianum, virens, atroviride or viride.

[0162] (Group N-UNE) A plant- or animal-derived drug containing a synthetic extract and an unrefined oil with an unknown or uncertain mode of action, preferably a plant- or animal-derived drug selected from azadirachtin, camellia seed cake, essential oil, garlic extract, pongamia oil, terpenes, such as carvacrol, and Quillaja saponaria extract.

[0163] Examples of herbicides that can be mixed with the compounds and compositions of the present invention are as follows: Acetochlor, Acifluorfen, Acifluorfen-methyl, Acifluorfen-sodium, Acifluorfen, Acifluorfen-methyl, Acifluorfen-sodium, Acronifen, Alachlor, Allidochlor, Alloxydim, Alloxydim-sodium, Ametryn, Amicarbazone, Amidochlor, Amidosulfuron, 4-Amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, Aminocyclopyrachlor, Aminocyclopyrachlor-potassium, Aminocyclopyrachlor-methyl, Aminopyralid, Aminopyralid-dimethylammonium, Aminopyralid-tripromine, Amitrole, Ammonium sulfamate, Anilophos, Asulam, Asulam-potassium, Asulam-sodium, Atrazine, Azafenidin, Azimsulfuron, Beflubutamid, (S)-(-)-Beflubutamid, Beflubutamid-M, Benazolin, Benazolin-ethyl, Benazolin-dimethylammonium, Benazolin-potassium, Benfluralin, Benfuresate, Bensulfuron, Bensulfuron-methyl, Bensulide, Bentazone, Bentazone-sodium, Benzobicyclon, Benzofenap, Bicyclopyrone, Bifenox, Bilanafos, Bilanafos-sodium, Bipyrazon, Bispyribac, Bispyribac-sodium, Bixlozone, Bromacil, Bromacil-lithium, Bromacil-sodium, Bromobutide, bromophenoxim, bromoxynil, bromoxynil-butyrate, -potassium, -heptanoate, and -octanoate, busoxinone, butachlor, butaphenil, butamiphos, butenachlor, butralin, butroxydim, butyrate, cafenstrole, camvbenzchlor, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chloramben-ammonium, chloramben-diolamine, chloramben-methyl, chloramben-methylammonium, chloramben-sodium, chlorobromuron, chlorfenac, chlorfenac-ammonium, chlorfenac-sodium, chlorfenprop, chlorfenprop-methyl, chlorflurenol, chlorflurenol-methyl, chloridazon, chlormequat, chlormequat-ethyl, chlorphthalim, chlorotoluron, chlorosulfuron, chlorothal, chlorothal-dimethyl, chlorothal-monomethyl, cinidon, cinidon-ethyl, cinmethylin, exo-(+)-cinmethylin, that is, (1R,2S,4S)-4-isopropyl-1-methyl-2-[(2-methoxybenzyl)oxy]-7-oxabicyclo[2.2.1]heptane, exo-(-)-cinmethylin, that is, (1R,2S,4S)-4-isopropyl-1-methyl-2-[(2-methoxybenzyl)oxy]-7-oxabicyclo[2.2.1]heptane, cinosulfuron, clathrim, clethodim, clodinafop, clodinafop-ethyl, clodinafop-propargyl, chromazone, chlormepropp, clopyralid, clopyralid-methyl, clopyralid-olamine, clopyralid-potassium, clopyralid-tripomine, chloransulam, chloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyranil, cyclopyrimorate, cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D (its ammonium, -butyl, -butyl, choline, dimethylammonium, -dimethylammonium, -diolamine, -doboxyl, -Dodecylammonium, etexyl, ethyl, 2-ethylhexyl, heptylammonium, isobutyl, isooctyl, isopropyl, isopropylammonium, lithium, meptyl, methyl, potassium, tetradecylammonium, triethylammonium, triisopropanolammonium, tripramine and trolamine salts), 2,4-DB, 2,4-DB-butyl, dimethylammonium, isooctyl, -potassium and -sodium, dimexron (dimexron), dalapon, dalapon-calcium, dalapon-magnesium, dalapon-sodium, dazomet, dazomet-sodium, n-decanol, 7-deoxy-D-sedoheptulose, desmedipham, detrityl-pyrazolate (DTP), dicamba and its salts, for example, dicamba-bipropiamine, dicamba-N,N-bis(3-aminopropyl)methylamine, dicamba-butyl, dicamba-choline, dicamba-diglycolamine, dicamba-dimethylammonium, dicamba-diethanolamineammonium, dicamba-diethylammonium, dicamba-isopropylammonium, dicamba-methyl, dicamba-monoethanolamine, dicamba-olamine, dicamba-potassium, dicamba-sodium, dicamba-triethanolamine, dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, dichlorprop, dichlorprop-butyl, Dichlorprop-dimethylammonium, Dichlorprop-ethoxyl, Dichlorprop-ethylammonium, Dichlorprop-isooctyl, Dichlorprop-methyl, Dichlorprop-potassium, Dichlorprop-sodium, Dichlorprop-P, Dichlorprop-P-dimethylammonium, Dichlorprop-P-ethoxyl, Dichlorprop-P-potassium, Dichlorprop-P-sodium, Dichlorvo, Dichlorvo-methyl, Dichlorvo-P, Dichlorvo-P-methyl, Diallate, Diphenzoate, Diphenzoate-methylsulfate, Diflufenican, Diflufenozopyr, Diflufenozopyr-sodium, Dimethametryn, Dimipipetate, Dimethosulfazet, Dimethachlor, Dimethametryn, Dimetenamid, Dimetenamid-P, Dimetrasulfuron, Dinoterb, Dinoterb-acetate, Diphenamid, Diquat, Diquat-dibromide, Diquat-dichloride, Dithiopyr, Diuron, DNOC, DNOC-ammonium, DNOC-potassium, DNOC-sodium, Endothal, endothal-diammonium, endothal-dipotassium, endothal-disodium, epirifenasyl (S-3100), EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethametsulfuron-methyl, ethidimuron, ethofumesate, ethoxyphene, ethoxyphene-ethyl, ethoxysulfuron, etobenzanid, F-5231, namely, N-{2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-4,5-dihydro-5-oxo-1H-tetrazol-1-yl]phenyl}ethanesulfonamide, F-7967, namely, 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxysulfone, fenpyrazon, fenquinotrione, fentrazamide, flamprop, flamprop-isopropyl, flamprop-methyl, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, flupirauxifen, flupirauxifen-benzyl, fluaquizip, fluaquizip-butyl, fluaquizip-methyl, fluaquizip-P, fluaquizip-P-butyl, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl Full metulam, full microchlorac, full microchlorac - pentyl, full mioxyazine, full omethuron, full lenol, full lenol - butyl, - dimethylammonium and - methyl, fluoroglycofen, fluoroglycofen - ethyl, full propanate, full propanate - sodium, full pyrasulfuron, full pyrasulfuron - methyl, full pyrasulfuron - methyl - sodium, full ridon, full rochloridone, full roxypyr, full roxypyr - butomethyl, full roxypyr - meptyl, full rutamon, full thiaacet, full thiaacet - methyl, homesaifen, homesaifen - sodium, horamsulfuron, horamsulfuron sodium salt, fosamine, fosamine - ammonium, glufosinate, glufosinate - ammonium, glufosinate - sodium, L - glufosinate - ammonium, L - glufosinate - sodium, glufosinate - P - sodium, glufosinate - P - ammonium, glyphosate, glyphosate - ammonium, - isopropylammonium, - diammonium, - dimethylammonium, - potassium, - sodium, sesquisodium and trimesium, H - 9201, that is, O-(2,4 - dimethyl - 6 - nitrophenyl)-O - ethyl - isopropylphosphoramidothioate, halauxifen, halauxifen - methyl, halosafen, halosulfuron, halosulfuron - methyl, haloxyfop, haloxyfop - P, haloxyfop - ethoxyethyl, haloxyfop - P - ethoxyethyl, haloxyfop - methyl, Haloxyfop-P-methyl, Haloxyfop-sodium, Hexazinone, HNPC-A8169, i.e., (2S)-2-{3-[(5-tert-butylpyridin-2-yl)oxy]phenoxy}propanoic acid prop-2-yn-1-yl, HW-02, i.e., 1-(dimethoxyphosphoryl)-ethyl-(2,4-dichlorophenoxy)acetate, Hydantoin, Imazamethabenz, Imazamethabenz-methyl, Imazamox, Imazamox-ammonium, Imazapic, Imazapic-ammonium, Imazapyr, Imazapyr-isopropylammonium, Imazakip, Imazakip-ammonium, Imazakip-methyl, Imazetapyr, Imazetapyr-inmonium, Imazosulfuron, Indanofan, Indaziflam, Iodosulfuron, Iodosulfuron-methyl, Iodosulfuron-methyl-sodium, Ioxynil, Ioxynil-lithium, -octanoate, -potassium and -sodium, Ipfencarbazone, Isoproturon, Isouron, Isoxaben, Isoxaflutole, Carbutilate, KUH-043, i.e., 3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole, Ketospiradox, Ketospiradox-potassium, Lactofen, Rankotriol, Lenacil, Linuron, MCPA, MCPA-butyl, -butyl, -dimethylammonium, -diolamine, -2-ethylhexyl, -ethyl, -isobutyl, -isopropyl, -isopropylammonium, -methyl, -olamine, -potassium, -sodium and -trolamine, MCPB, MCPB-methyl, -ethyl and -sodium, Mecoprop, Mecoprop-butyl, Mecoprop-dimethylammonium, Mecoprop-diolamine, Mecoprop-ethoxyl, Mecoprop-ethazil, Mecoprop-isooctyl, Mecoprop-methyl, Mecoprop-potassium, Mecoprop-sodium, and Mecoprop-trolamine, Mecoprop-P, Mecoprop-P-butyl, -dimethylammonium, -2-ethylhexyl, and -potassium, Mefenacet, Mefluidide, Mefluidide-diolamine,Mefluidide-potassium, mesosulfuron, mesosulfuron-methyl, mesosulfuron sodium salt, mesotrione, metobenzthiazuron, metam, metamifop, metazachlor, metazosulfuron, metobenzthiazuron, methiopyrsulfuron, methiozolin, methyl isothiocyanate, metobromuron, metachlor, S-metachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinate, monolinuron, monosulfuron, monosulfuron-methyl, MT-5950, i.e., N-[3-chloro-4-(1-methylethyl)phenyl]-2-methylpentanamide, NGGC-011, napropamide, NC-310, i.e., 4-(2,4-dichlorobenzoyl)-1-methyl-5-benzyloxypyrazole, NC-656, i.e., 3-[(isopropylsulfonyl)methyl]-N-(5-methyl-1,3,4-oxadiazol-2-yl)-5-(trifluoromethyl)[1,2,4]triazolo[4,3-a]pyridine-8-carboxamide, neburon, nicosulfuron, nonanoic acid (pelargonic acid), norflurazon, oleic acid (fatty acid), oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxadiquofop, oxyfluorfen, paraquat, paraquat dichloride, paraquat dimethyl sulfate, pebulate, pendimethalin, penoxsulam, pentachlorophenol, pentoxazone, petoxamid, petroleum, fenmedifam, fenmedifam-ethyl, picloram, picloram dimethylammonium, picloram etexyl, picloram isooctyl, picloram methyl, picloram olamine, picloram potassium, picloram triethylammonium, picloram tripromine, picloram trolamine, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometrin, propachlor, propanil, propaquizafop, propazine, propanil, propisochlor, propoxycarbazone, propoxycarbazone sodium, propyrisulfuron, propyzamide,prosulcarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrazosulfotole, pyrazolate, pyrazosulfuron, pyrazosulfuron-ethyl, pyraoxyphen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriflutalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxasulam, quinclorac, quinclorac-dimethylammonium, quinclorac-methyl, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, QYM201, that is, 1-{2-chloro-3-[(3-cyclopropyl-5-hydroxy-1-methyl-1H-pyrazol-4-yl)carbonyl]-6-(trifluoromethyl)phenyl}piperidin-2-one, rimsulfuron, sulfofenacil, sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrione, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron, SYP-249, that is, 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate, SYP-300, that is, 1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidine-4,5-dione, 2,3,6-TBA, TCA (trichloroacetic acid) and its salts, for example, TCA-ammonium, TCA-calcium, TCA-ethyl, TCA-magnesium, TCA-sodium, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbuthylazine, terbutryn, terbuthylazine, terbutryn, tetflupyrolimet, saxtoxmin, tenilchlor, thiazopyr, thienecarbazone, thienecarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, thiafenox, topramezone, traloxydim, triafamone, tri-allate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, triclopyr-butotyl, triclopyr-choline, triclopyr-ethyl, triclopyr-triethylammonium, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, triflumizole, trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea sulfate, vernolate, XDE-848, ZJ-0862, that is, 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline, Ethyl 3-(2-chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydropyrimidin-1(2H)-yl)phenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylate, ethyl [(3-{2-chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}pyridin-2-yl)oxy]acetate, 3-chloro-2-[(3-(difluoromethyl)isoxazol-5-yl]phenyl-5-chloropyrimidin-2-yl ether, 2-(3,4-dimethoxyphenyl)-4-[(2-hydroxy-6-oxosoclohex-1-en-1-yl)carbonyl]-6-methylpyridazin-3(2H)-one, 2-({2-[(2-methoxyethoxy)methyl]-6-methylpyridin-3-yl}carbonyl)cyclohexane-1,3-dione, (5-hydroxy-1-methyl-1H-pyrazol-4-yl)(3,3,4-trimethyl-1,1-dioxide-2,3-dihydro-1-benzothiophen-5-yl)methanone, 1-methyl-4-[(3,3,4-trimethyl-1,1-dioxide-2,3-dihydro-1-benzothiophen-5-yl)carbonyl]-1H-pyrazol-5-yl propane-1-sulfonate, 4-{2-chloro-3-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]-4-(methylsulfonyl)benzoyl}-1-methyl-1H-pyrazol-5-yl-1,3-dimethyl-1H-pyrazole-4-carboxylate;4-Amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid cyanomethyl, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid prop-2-yn-1-yl, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid methyl, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid benzyl, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylic acid ethyl, 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1-isobutyryl-1H-indol-6-yl)pyridine-2-; Methyl carboxylic acid, methyl 6-(1-acetyl-7-fluoro-1H-indol-6-yl)-4-amino-3-chloro-5-fluoropyridine-2-carboxylate, methyl 4-amino-3-chloro-6-[1-(2,2-dimethylpropanoyl)-7-fluoro-1H-indol-6-yl]-5-fluoropyridine-2-carboxylate, methyl 4-amino-3-chloro-5-fluoro-6-[7-fluoro-1-(methoxyacetyl)-1H-indol-6-yl]pyridine-2-carboxylate, potassium 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate, sodium 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate, butyl 4-amino-3-chloro-5-fluoro-6-(7-fluoro-1H-indol-6-yl)pyridine-2-carboxylate, 4-hydroxy-1-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolidin-2-one, 3-(5-tert-butyl-1,2-oxazol-3-yl)-4-hydroxy-1-methylimidazolidin-2-one, 3-[5-chloro-4-(trifluoromethyl)pyridin-2-yl]-4-hydroxy-1-methylimidazolidin-2-one, 4-hydroxy-1-methoxy-5-methyl-3-[4-(trifluoromethyl)pyridin-2-yl]imidazolidin-2-one, 6-[(2-hydroxy-6-oxocyclohex-1-en-1-yl)carbonyl]-1,5-dimethyl-3-(2-methylphenyl)quinazoline-2,4(1H,3H)-dione, 3-(2,6-dimethylphenyl)-6-[(2-hydroxy-6-oxocyclohex-1-en-1-yl)carbonyl]-1-methylquinazoline-2,4(1H,3H)-dione, 2-[2-chloro-4-(methylsulfonyl)-3-(morpholin-4-ylmethyl)benzoyl]-3-hydroxycyclohex-2-en-1-one, 1-(2-carboxyethyl)-4-(pyrimidin-2-yl)pyridazin-1-ium salts (with anions such as chloride, acetate or trifluoroacetate), 1-(2-carboxyethyl)-4-(pyridazin-3-yl)pyridazin-1-ium salts (with anions such as chloride, acetate or trifluoroacetate), 4-(pyrimidin-2-yl)-1-(2-sulfoethyl)pyridazin-1-ium salts (with anions such as chloride, acetate or trifluoroacetate), 4-(pyridazin-3-yl)-1-(2-sulfoethyl)pyridazin-1-ium salts (with anions such as chloride, acetate or trifluoroacetate), 1-(2-carboxyethyl)-4-(1,3-thiazol-2-yl)pyridazin-1-ium salts (with anions such as chloride, acetate or trifluoroacetate), 1-(2-carboxyethyl)-4-(1,3-thiazol-2-yl)pyridazin-1-ium salts (with anions such as chloride, acetate or trifluoroacetate).

[0164] Examples of plant growth regulators that can be mixed with the compounds and compositions of the present invention are as follows: Abscisic acid and related analogs [e.g., (2Z,4E)-5-[6-ethynyl-1-hydroxy-2,6-dimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid, methyl (2Z,4E)-5-[6-ethynyl-1-hydroxy-2,6-dimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoate, (2Z,4E)-3-ethyl-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)penta-2,4-dienoic acid, (2E,4E)-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-(trifluoromethyl)penta-2,4-dienoic acid, methyl (2E,4E)-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-(trifluoromethyl)penta-2,4-dienoate, (2Z,4E)-5-(2-hydroxy-1,3-dimethyl-5-oxobicyclo[4.1.(Hepta-3-en-2-yl)-3-methylpenta-2,4-dienoic acid, acibenzolar, acibenzolar-S-methyl, S-adenosylhomocysteine, allantoin, 2-aminoethoxyvinylglycine (AVG), aminooxyacetic acid and related esters [e.g., (isopropylidene)-aminooxyacetic acid-2-(methoxy)-2-oxoethyl ester, (isopropylidene)-aminooxyacetic acid-2-(hexyloxy)-2-oxoethyl ester, (cyclohexylidene)-aminooxyacetic acid-2-(isopropyloxy)-2-oxoethyl ester], 1-aminocyclopropane-1-carboxylic acid and its derivatives, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, bikinin, brassinolide, brassinolide-ethyl, L-canavanine, catechin and catechins (e.g., (2S,3R)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol), chito-oligosaccharide (CO; CO is different from LCO in that they do not have the fatty acid pendant molecular chains characteristic of LCO. CO is called N-acetylchito-oligosaccharide and consists of GlcNAc residues, but the chitin molecule [(C. 8 H 13 NO 5 )n, CAS No. 1398-61-4] and the chitosan molecule [(C 5 H 11 NO 4) having a side-chain modification different from that of n, CAS No. 9012-76-4), chitinous compounds, chloromethicone, clopropp, cyclanilide, 3-(cycloprop-1-enyl)propionic acid, 1-[2-(4-cyano-3,5-dicyclopropylphenyl)acetamido]cyclohexanecarboxylic acid, 1-[2-(4-cyano-3-cyclopropylphenyl)acetamido]cyclohexanecarboxylic acid, daminozide, dazomet, dazomet-sodium, n-decanol, dicamba, dicamba-sodium, endothal, endothal-dipotassium, -disodium, and -mono(N,N-dimethylalkylammonium), ethephon, flumetralin, flurenol, flurenol-butyl, flurenol-methyl, flurprimidol, chlorfenuron, gibberellic acid, inabenfide, indole-3-acetic acid (IAA), 4-indol-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid or its derivatives (e.g., methyl jasmonate, ethyl jasmonate), lipochitooligosaccharides (LCO, also called common nodulation (Nod) signals (or nod factors) or Myc factors, consisting of an oligosaccharide backbone of β-1,4-linked N-acetyl-D-glucosamine ("GlcNAc) residues having an N-linked fatty acyl chain condensed at the non-reducing end.As is understood in the art, LCOs differ in the number of GlcNAc residues in the main chain, the length and degree of saturation of the fatty acyl chains, and the substitution of the reducing or non-reducing sugar residues), linoleic acid or its derivatives, linolenic acid or its derivatives, maleic hydrazide, mepiquat chloride, mepiquat pentaborate, 1-methylcyclopropene, 3-methylcyclopropene, 1-ethylcyclopropene, 1-n-propylcyclopropene, 1-cyclopropenylmethanol, methoxyvinylglycine (MVG), 3'-methylabscisic acid, 1-(4-methylphenyl)-N-(2-oxo-1-propyl-1,2,3,4-tetrahydroquinolin-6-yl)methanesulfonamide and related substituted tetrahydroquinolin-6-yl)methanesulfonamide, (3E,3aR,8bS)-3-({[(2R)-4-methyl-5-oxo-2,5-dihydrofuran-2-yl]oxy}methylene)-3,3a,4,8b-tetrahydro-2H-inden[1,2-b]furan-2-one and related lactones outlined in European Patent Application Publication No. 2248421, 2-(1-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenolate mixture, 4-oxo-4[(2-phenylethyl)amino]butyric acid, paclobutrazol, 4-phenylbutyric acid and its related salts (e.g., sodium 4-phenylbutanoate, potassium 4-phenylbutanoate), phenylalanine, N-phenylphthalamic acid, prohexadione, prohexadione-calcium, putrescine, prohydrojasmon, lysovitoxin, salicylic acid, methyl salicylate, sarcosine, sodium cyclopropa-1-en-1-ylacetate, sodium cyclopropa-2-en-1-ylacetate, sodium 3-(cyclopropa-2-en-1-yl)propanoate, sodium 3-(cyclopropa-1-en-1-yl)propanoate, sodefungin, spermidine, spermine, strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tryptophan, chitodef, uniconazole, uniconazole-P, 2-fluoro-N-(3-methoxyphenyl)-9H-purin-6-amine.

[0165] Examples of phytotoxicity reducing agents that can be mixed with the compounds and compositions of the present invention are as follows in S1) to S16): S1) Compounds from the group of heterocyclic carboxylic acid derivatives: S1 a ) Compounds of the dichlorophenylpyrazoline-3-carboxylic acid type (S1 a ) Preferably, 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylic acid, ethyl 1-(2,4-dichlorophenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazoline-3-carboxylate (S1-1) ("mefenpyr diethyl"), and compounds such as related compounds described in WO 91 / 07874; S1 b ) Derivatives of dichlorophenylpyrazolecarboxylic acid (S1 b ) Preferably, ethyl 1-(2,4-dichlorophenyl)-5-methylpyrazole-3-carboxylate (S1-2), ethyl 1-(2,4-dichlorophenyl)-5-isopropylpyrazole-3-carboxylate (S1-3), ethyl 1-(2,4-dichlorophenyl)-5-(1,1-dimethylethyl)pyrazole-3-carboxylate (S1-4), and compounds such as related compounds described in EP 333131 and EP 269806; S1 c ) Derivatives of 1,5-diphenylpyrazole-3-carboxylic acid (S1 c ) Preferably, ethyl 1-(2,4-dichlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-5), methyl 1-(2-chlorophenyl)-5-phenylpyrazole-3-carboxylate (S1-6), and compounds such as related compounds described in EP 268554; S1 d ) Compounds of the triazolecarboxylic acid type (S1 d) Preferably, compounds such as fenchlorazole (ethyl ester), i.e., ethyl 1-(2,4-dichlorophenyl)-5-trichloromethyl-1H-1,2,4-triazole-3-carboxylate (S1-7), and related compounds described in European Patent Application Publication No. 174562 and European Patent Application Publication No. 346620; S1 e ) Compounds of the 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid type (S1 e ) Preferably, compounds such as ethyl 5-(2,4-dichlorophenyl)-2-isoxazoline-3-carboxylate (S1-8) or ethyl 5-phenyl-2-isoxazoline-3-carboxylate (S1-9) and related compounds described in International Publication No. 91 / 08202, or 5,5-diphenyl-2-isoxazolinecarboxylic acid (S1-10) or ethyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-11) (「isoxadifen-ethyl」) or n-propyl 5,5-diphenyl-2-isoxazoline-3-carboxylate (S1-12) or ethyl 5-(4-fluorophenyl)-5-phenyl-2-isoxazoline-3-carboxylate (S1-13) described in International Publication No. 95 / 07897. S2) Compounds from the group of 8-quinolinoxy derivatives (S2): S2 a ) Compounds of the 8-quinolinoxyacetic acid type (S2 a) Preferably, 1-methylhexyl (5-chloro-8-quinolinoxy) acetate (“cloquintocet - mexyl”) (S2-1), 1,3-dimethylbutan-1-yl (5-chloro-8-quinolinoxy) acetate (S2-2), 4-allyloxybutyl (5-chloro-8-quinolinoxy) acetate (S2-3), 1-allyloxyprop-2-yl (5-chloro-8-quinolinoxy) acetate (S2-4), ethyl (5-chloro-8-quinolinoxy) acetate (S2-5), methyl (5-chloro-8-quinolinoxy) acetate (S2-6), allyl (5-chloro-8-quinolinoxy) acetate (S2-7), 2-(2-propylideneiminooxy)-1-ethyl (5-chloro-8-quinolinoxy) acetate (S2-8), 2-oxoprop-1-yl (5-chloro-8-quinolinoxy) acetate (S2-9) and related compounds described in European Patent Application Publication No. 86750, European Patent Application Publication No. 94349 and European Patent Application Publication No. 191736 or European Patent Application Publication No. 0492366; furthermore, (5-chloro-8-quinolinoxy) acetic acid (S2-10), hydrates and salts thereof, for example, its lithium salt, sodium salt, potassium salt, calcium salt, magnesium salt, aluminum salt, iron salt, ammonium salt, quaternary ammonium salt, sulfonium salt or phosphonium salt described in International Publication No. 2002 / 34048; S2 b )(5-chloro-8-quinolinoxy) malonic acid type compounds (S2 b ) Preferably, compounds such as diethyl (5-chloro-8-quinolinoxy) malonate, diallyl (5-chloro-8-quinolinoxy) malonate, methyl ethyl (5-chloro-8-quinolinoxy) malonate and related compounds described in European Patent Application Publication No. 0582198. (S3) Active compounds of the dichloroacetamide type (soil-acting phytotoxicity reducing agents) that are frequently used as phytotoxicity reducing agents to be used before germination, for example, "dichloromid" (N,N-diallyl-2,2-dichloroacetamide) (S3-1), "R-29148" from Stauffer (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) (S3-2), "R-28725" from Stauffer (3-dichloroacetyl-2,2-dimethyl-1,3-oxazolidine) (S3-3), "benoxacor" (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4), "PPG-1292" from PPG Industries (N-allyl-N-[(1,3-dioxolan-2-yl)methyl]dichloroacetamide) (S3-5), "DKA-24" from Sagro-Chem (N-allyl-N-[(allylaminocarbonyl)methyl]dichloroacetamide) (S3-6), "AD-67" or "MON4660" from Nitrokemia or Monsanto (3-dichloroacetyl-1-oxa-3-azaspiro[4.5]decane) (S3-7), "TI-35" from TRI-Chem RT (1-dichloroacetylazepane) (S3-8), "Diclonon" (dicyclonon) or "BAS145138" or "LAB145138" (S3-9), ((RS)-1-dichloroacetyl-3,3,8a-trimethylperhydro-1H-pyrrolo[1,2-a]pyrimidin-6-one) from BASF, "furilazole" or "MON13900" ((RS)-3-dichloroacetyl-5-(2-furyl)-2,2-dimethyloxazolidine) (S3-10), and its (R) isomer (S3-11). (S4) Compounds from the classification of acylsulfonamides (S4): S4 a ) N-acylsulfonamides and their salts described in International Publication No. WO 97 / 45016, S4 b ) Compounds corresponding to 4-(benzoylsulfamoyl)benzamide and their salts described in International Publication No. WO 99 / 16744, S4 c) Compounds from the classification of benzoylsulfamoylphenylureas described in European Patent Application Publication No. 365484, for example, 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3-methylurea, 1-[4-(N-2-methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylurea and 1-[4-(N-4,5-dimethylbenzoylsulfamoyl)phenyl]-3-methylurea; S4 d ) for example, N-phenylsulfonylterephthalamide type compounds and salts thereof known from Chinese Patent Application Publication No. 101838227. S5) Active compounds (S5) from the classification of hydroxyaromatic compounds and aromatic-aliphatic carboxylic acid derivatives, for example, ethyl 3,4,5-triacetoxybenzoate, 3,5-dimethoxy-4-hydroxybenzoic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid described in International Publication No. 2004 / 084631, International Publication No. 2005 / 015994, International Publication No. 2005 / 016001. S6) Activity (S6) from the classification of 1,2-dihydroquinoxalin-2-ones, for example, 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one, 1-methyl-3-(2-thienyl)-1,2-dihydroquinoxalin-2-thione, 1-(2-aminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one hydrochloride, 1-(2-methylsulfonylaminoethyl)-3-(2-thienyl)-1,2-dihydroquinoxalin-2-one described in International Publication No. 2005 / 112630. S7) Compounds (S7) from the classification of diphenylmethoxyacetic acid derivatives, for example, methyl diphenylmethoxyacetate (CAS registration number 41858-19-9) (S7-1), ethyl diphenylmethoxyacetate or diphenylmethoxyacetic acid described in International Publication No. 98 / 38856. S8) 2-Fluoroacrylic acid derivatives described in International Publication No. 98 / 27049. S9) Active compounds (S9) from the classification of 3-(5-tetrazolylcarbonyl)-2-quinolone, for example, 1,2-dihydro-4-hydroxy-1-ethyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS registration number 219479-18-2), 1,2-dihydro-4-hydroxy-1-methyl-3-(5-tetrazolylcarbonyl)-2-quinolone (CAS registration number 95855-00-8), as described in International Publication No. 99 / 000020 (WO-A-199 / 000020). S10) N-acylsulfonamides as described in International Publication No. 2007 / 023719 and International Publication No. 2007 / 023764. S11) Active compounds (S11) of the oxime-imino compound type known as seed dressing agents, for example, "Oxabetrinil" ((Z)-1,3-dioxolan-2-ylmethoxyimino(phenyl)acetonitrile) (S111), known as a seed dressing phytotoxicity reducing agent for millet / sorghum against metolachlor damage, "Fluxofenim" (1-(4-chlorophenyl)-2,2,2-trifluoro-1-ethanone-O-(1,3-dioxolan-2-ylmethyl)oxime) (S11-2), known as a seed dressing phytotoxicity reducing agent for millet / sorghum against metolachlor damage, and "Ciametrinil" or "CGA-43089" ((Z)-cyanomethoxyimino(phenyl)acetonitrile) (S11-3), known as a seed dressing phytotoxicity reducing agent for millet / sorghum against metolachlor damage. S12) Active compounds (S12) from the classification of isothiochromanone, for example, methyl [(3-oxo-1H-2-benzothiopyran-4(3H)-ylidene)methoxy]acetate (CAS registration number 205121-04-6) (S12-1) and related compounds from International Publication No. 1998 / 13361. S13) One or more compounds (S13) from the group: "Naphthalic anhydride" (1,8-naphthalenedicarboxylic anhydride) (S13-1), known as a seed coating phytotoxicity reducer for corn against thiocarbamate herbicide damage; "Fenchlorim" (4,6-dichloro-2-phenylpyrimidine) (S13-2), known as a phytotoxicity reducer for pretilachlor in sown rice; "Flurazole" (benzyl 2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate) (S13-3), known as a seed coating phytotoxicity reducer for foxtail millet / sorghum against alachlor and metolachlor damage; "CL304415" from American Cyanamid (CAS registration number 31541-57-8) (4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4), known as a phytotoxicity reducer for corn against damage by imidazolinones; "MG191" from Nitrokemia (CAS registration number 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5), known as a phytotoxicity reducer for corn; "MG-838" from Nitrokemia (CAS registration number 133993-74-5) (2-propenyl 1-oxa-4-azaspiro[4.5]decane-4-carbodithioate) (S13-6); "Disulfoton" (O,O-diethyl S-2-ethylthioethyl phosphorodithioate) (S13-7); "Dietholate" (O,O-diethyl O-phenyl phosphorothioate) (S13-8); "Mephenate" (4-chlorophenyl methylcarbamate) (S13-9), which are known as substances for reducing phytotoxicity for crops such as rice in addition to their herbicidal effects on weeds. S14) Active compounds that, in addition to their herbicidal action against weeds, also have a phytotoxicity reducer action on crops such as rice, for example "Dimpeperate" or "MY-93" (S-1-methyl-1-phenylethyl piperidine-1-carbothioate), which is known as a phytotoxicity reducing agent for rice damaged by the herbicide molinate, "Daimuron" or "SK23" (1-(1-methyl-1-phenylethyl)-3-p-tolylurea), which is known as a phytotoxicity reducing agent for rice against imazosulfuron herbicide damage, "Cumiluron" = "JC-940" (3-(2-chlorophenylmethyl)-1-(1-methyl-1-phenylethyl)urea, see JP-A-60-087254), which is known as a phytotoxicity reducing agent for rice against some herbicides, "Methoxyphenone" or "NK049" (3,3'-dimethyl-4-methoxybenzophenone), which is known as a phytotoxicity reducing agent for rice against some herbicides, and "CSB" (1-bromo-4-(chloromethylsulfonyl)benzene) (CAS registration number 54091-06-4) from Kumiai, which is known as a phytotoxicity reducing agent for rice against some herbicides. S15) Pyridine-2-oxy-3-carboxamides as described in International Publication No. 2008 / 131861 and International Publication No. 2008 / 131860. S16) Active compounds that are mainly used as herbicides but also have a phytotoxicity reducing effect on crop plants, for example, (2,4-dichlorophenoxy)acetic acid (2,4-D), (4-chlorophenoxy)acetic acid, (R,S)-2-(4-chloro-o-tolyloxy)propionic acid (mecoprop), 4-(2,4-dichlorophenoxy)butyric acid (2,4-DB), (4-chloro-o-tolyloxy)acetic acid (MCPA), 4-(4-chloro-o-tolyloxy)butyric acid, 4-(4-chlorophenoxy)butyric acid, 3,6-dichloro-2-methoxybenzoic acid (dicamba), 3,6-dichloro-2-methoxybenzoic acid 1-(ethoxycarbonyl)ethyl (lactidichlor-ethyl).

[0166] Examples of nitrification inhibitors that can be mixed with the compounds and compositions of the present invention are selected from the group consisting of: 2-(3,4-dimethyl-1H-pyrazol-1-yl)succinic acid, 2-(4,5-dimethyl-1H-pyrazol-1-yl)succinic acid, 3,4-dimethylpyrazolium glycolate, 3,4-dimethylpyrazolium citrate, 3,4-dimethylpyrazolium lactate, 3,4-dimethylpyrazolium mandelate, 1,2,4-triazole, 4-chloro-3-methylpyrazole, N-((3(5)-methyl-1H-pyrazol-1-yl)methyl)acetamide, N-((3(5)-methyl-1H-pyrazol-1-yl)methyl)formamide, N-((3(5),4-dimethylpyrazol-1-yl)methyl)formamide, N-((4-chloro-3(5)-methyl-pyrazol-1-yl)methyl)formamide;Reaction adducts of dicyandiamide, urea and formaldehyde, triazonyl-formaldehyde-dicyandiamide adducts, 2-cyano-1-((4-oxo-1,3,5-triazinane-1-yl)methyl)guanidine, 1-((2-cyanoguanidino)methyl)urea, 2-cyano-1-((2-cyanoguanidino)methyl)guanidine, 2-chloro-6-(trichloromethyl)-pyridine (nitrapyrin or N-Serve), dicyandiamide, 3,4-dimethylpyrazole phosphate, 4,5-dimethylpyrazole phosphate, 3,4-dimethylpyrazole, 4,5-dimethylpyrazole, ammonium thiosulfate, neem, neem-based products, linoleic acid, α-linolenic acid, methyl p-coumarate, methyl ferulate, methyl 3-(4-hydroxyphenyl)propionate, karanjin, brachialactone, p-benzoquinone sorgoleone, 4-amino-1,2,4-triazole hydrochloride, 1-amido-2-thiourea, 2-amino-4-chloro-6-methylpyrimidine, 2-mercapto-benzothiazole, 5-ethoxy-3-trichloromethyl-1,2,4-thiadiazole (terrazole, etridiazole), 2-sulfanylamidothiazole, 3-methylpyrazole, 1,2,4-triazole thiourea, cyanamide, melamine, zeolite powder, catechol, benzoquinone, sodium tetraborate, allylthiourea, chlorate, and zinc sulfate.;

[0167] The compounds and compositions of the present invention may be combined with one or more agriculturally beneficial agents.

[0168] Examples of agents having pesticidal effects include biostimulants, plant growth regulators, plant signal molecules, growth promoters, microbial stimulatory molecules, biomolecules, soil conditioners, nutrients, plant nutrient promoters, and others, such as lipochitooligosaccharide (LCO), chitooligosaccharide (CO), chitinous compounds, flavonoids, jasmonic acid or its derivatives (e.g., jasmonic acid esters), cytokinins, auxins, gibberellins, abscisic acid, ethylene, brassinosteroids, salicylates, macronutrients and micronutrients, linoleic acid or its derivatives, linolenic acid or its derivatives, karrikins, and effective microorganisms (e.g., Rhizobium spp., Bradyrhizobium spp., Sinorhizobium spp., Azorhizobium spp, Glomus spp., Gigaspora spp., Hymenoscyphous spp., Oidiodendron spp., Laccaria spp., Pisolithus spp., Rhizopogon spp., Scleroderma spp., Rhizoctonia spp., Acinetobacter spp., Arthrobacter spp., Arthrobotrys spp., Aspergillus spp., Azospirillum spp., Bacillus spp., Burkholderia spp., Candida spp., Chryseomonas spp., Enterobacter spp., Eupenicillium spp., Exiguobacterium spp., Klebsiella spp., Kluyvera spp.) Microbacterium spp., Mucor spp., Paecilomyces spp., Paenibacillus spp., Penicillium spp., Pseudomonas spp., Serratia spp., Stenotrophomonas spp., Streptomyces spp., Streptosporangium spp., Swaminathania spp., Thiobacillus spp., Torulospora spp., Vibrio spp., Xanthobacter spp., Xanthomonas spp., others), and combinations thereof are included.

[0169] According to some embodiments, the compounds and compositions of the present invention may be combined with one or more biostimulants. The biostimulants may promote metabolic or physiological processes such as respiration, photosynthesis, nucleic acid uptake, ion uptake, nutrient delivery, or combinations thereof. Non-limiting examples of biostimulants that may be included in or used with the compositions of the present invention include seaweed extracts (e.g., Ascophyllum nodosum; BAYFOLAN ALGAE, Aglukon GmbH, Germany), bacterial extracts (e.g., extracts of one or more diazotrophs, phosphate-solubilizing microorgafjaponisms and / or biopesticides), fungal extracts, humic acids (e.g., potassium humate), fulvic acids, myo-inositol, and / or glycine, protein hydrolysates and amino acids and plant sources from both animal BAYFOLAN AMBITION&BAYFOLAN copper, SICIT, Italy, inorganic compounds (e.g., silica) and combinations thereof. According to some embodiments, the biostimulant is one or more Azospirillum extracts (e.g., an extract of a medium comprising A. brasilense INTA Az-39), one or more Bradyrhizobium extracts (e.g., B. elkanii SEMIA501, B. elkanii SEMIA 587, B. elkanii SEMIA 5019, B. japonicum NRRL B-50586 (also deposited as NRRL B-59565), B. japonicum NRRL B-50587 (also deposited as NRRL B-59566), B. japonicum NRRL B-50588 (also deposited as NRRL B-59567), B. japonicum NRRL B-50589 (also deposited as NRRL B-59568), B. japonicum NRRL B-50590 (also deposited as NRRL B-59569), B. japonicum NRRL B-50591 (also deposited as NRRL B-59570), B. japonicum NRRL B-50592 (also deposited as NRRL B-59571), B. japonicum NRRL B-50593 (also deposited as NRRL B-59572) B. japonicum NRRL B-50594 (also deposited as NRRL B-50493), B. japonicum NRRL B-50608, B. japonicum NRRL B-50609, B. japonicum NRRL B-50610, B. japonicum NRRL B-50611, B. japonicum NRRL B-50612, B. japonicum NRRL B-50726, B. japonicum NRRL B-50727, B. japonicum NRRL B-50728, B. japonicum NRRL B-50729, B. japonicum NRRL B-50730, B. japonicum SEMIA 566, B. japonicum SEMIA 5079, B. japonicum SEMIA 5080, B. japonicum USDA 6, B. japonicum USDA 110, B. japonicum USDA 122, B. japonicum USDA 123, B. japonicum USDA 127, B. japonicum USDA 129 and / or B. japonicum USDA 532C), one or more extracts (e.g., Rhizobium extract (e.g., extract of a medium comprising R. leguminosarum SO12A-2), one or more Sinorhizobium extracts (e.g., extract of a medium comprising S. fredii CCBAU114 and / or S. fredii USDA 205), one or more Penicillium extracts (e.g., P. bilaiae ATCC 18309, P. bilaiae (P.P. bilaiae ATCC 20851, P. bilaiae ATCC 22348, P. bilaiae NRRL 50162, P. bilaiae NRRL 50169, P. bilaiae NRRL 50776, P. bilaiae NRRL 50777, P. bilaiae NRRL 50778, P. bilaiae NRRL 50777, P. bilaiae NRRL 50778, P. bilaiae NRRL 50779, P. bilaiae NRRL 50780, P. bilaiae NRRL 50781, P. bilaiae NRRL 50782, P. bilaiae NRRL 50783, P. bilaiae NRRL 50784, P. bilaiae NRRL 50785, P. bilaiae NRRL 50786, P. bilaiae NRRL 50787, P. bilaiae NRRL 50788, P. bilaiae RS7B-SD1, P. brevicompactum AgRF18, P. canescens ATCC 10419, P. expansum ATCC 24692, P. Extracts of a medium comprising P. expansum YT02, P. fellutanum ATCC 48694, P. gaestrivorus NRRL 50170, P. glabrum DAOM 239074, P. glabrum CBS 229.28, P. janthinellum ATCC 10455, P. lanosocoeruleum ATCC 48919, P. radicum ATCC 201836, P. radicum FRR 4717, P. radicum FRR 4719, P. radicum N93 / 47267 and / or P. raistrickii ATCC 10490), one or more Pseudomonas extracts (e.g., an extract of a medium comprising P. jessenii PS06), one or more acaricidal, insecticidal and / or nematicidal extracts (e.g., an extract of a medium comprising Bacillus firmus I-1582, Bacillus mycoides AQ726, NRRL B-21664; Beauveria bassiana ATCC-74040, Beauveria bassiana ATCC-74250, Burkholderia sp. A396 sp. nov. linocensis (nov.rinojensis), NRRL B-50319, Chromobacterium subtsugae NRRL B-30655, Chromobacterium vaccinii NRRL B-50880, Flavobacterium H492, NRRL B-50584, Metarhizium anisopliae F52 (Metarhizium anisopliae strain 52, Metarhizium anisopliae strain 7, Metarhizium anisopliae strain 43 and Metarhizium anisopliae BIO-1020, TAE-001 also known as; deposited as DSM 3884, DSM 3885, ATCC 90448, SD 170 and ARSEF 7711) and / or Paecilomyces fumosoroseus FE991), and / or one or more antifungal extracts (e.g., an extract of a medium comprising Ampelomyces quisqualis AQ 10 (registered trademark) (Intrachem Bio GmbH&Co.KG, Germany), Aspergillus flavus AFLA-GUARD (registered trademark) (Syngenta Crop Protection, Inc., Switzerland),. Aureobasidium pullulans BOTECTOR® (bio-ferm GmbH, Germany), Bacillus pumilus AQ717 (NRRL B-21662), Bacillus pumilus NRRL B-30087, V(Bacillus) AQ175 (ATCC 55608), Bacillus AQ177 (ATCC 55609), Bacillus subtilis AQ713 (NRRL B-21661), Bacillus subtilis AQ743 (NRRL B-21665), Bacillus amyloliquefaciens FZB24, Bacillus amyloliquefaciens NRRL B-50349, Bacillus amyloliquefaciens TJ1000 (also known as 1BE, isolate ATCC BAA-390), Bacillus thuringiensis AQ52 (NRRL B-21619), Candida oleophila I-82 (e.g., ASPIRE®, Ecogen Inc., USA), Candida saitoana BIOCURE® (mixture with lysozyme BASF, USA) and BIOCOAT® (ArystaLife Science, Ltd., Cary, NC), Clonostachys rosea f. catenulata (also known as Gliocladium catenulatum) J1446 (PRESTOP®, Verdera, Finland), Coniothyrium minitans CONTANS® (Prophyta, Germany), Cryphonectria parasitica (CNICM, France), Cryptococcus albidus YIELD PLUS® (Anchor Bio-Technologies, South Africa), Fusarium oxysporum BIOFOX® (S.I.A.P.A., Italy) and FUSACLEAN® (Natural Plant Protection, France), Metschnikowia fructicola SHEMER® (Agrogreen, Israel), Microdochium dimerum ANTIBOT® (Agrauxine, France), Muscodor albus NRRL 30547, Muscodor roseus NRRL 30548, Phlebiopsis gigantea ROTSOP® (Verdera, Finland), Pseudozyma flocculosa SPORODEX® (Plant Products Co. Ltd., Canada), Pythium oligandrum DV74 (POLYVERSUM (registered trademark), Remeslo SSRO, Biopreparaty, Czech Republic), Reynoutria sachlinensis (e.g., REGALIA (registered trademark) Marrone BioInnovations, USA), Streptomyces NRRL B-30145, Streptomyces M1064, Streptomyces galbus NRRL 30232, Streptomyces lydicus WYEC 108 (ATCC 55445), Streptomyces violaceusniger YCED 9 (ATCC 55660; DE-THATCH-9 (registered trademark), DECOMP-9 (registered trademark) and THATCH CONTROL (registered trademark), Idaho Research Foundation, USA), Streptomyces WYE 53 (ATCC 55750; DE-THATCH-9 (registered trademark), DECOMP-9 (registered trademark) and THATCH CONTROL (registered trademark), Idaho Research Foundation, USA), Talaromyces flavus V117b (PROTUS (registered trademark), Prophyta, Germany), Trichoderma asperellum SKT-1 (ECO-HOPE (registered trademark), Kumiai Chemical Industry Co., Ltd., Japan), Trichoderma atroviride LC52 (SENTINEL (registered trademark), Agrimm Technologies Ltd, New Zealand), Trichoderma harzianum T-22 (PLANTSHIELD (registered trademark). , BioWorks Inc., USA), Trichoderma harzianum TH-35 (ROOT PRO®, Mycontrol Ltd., Israel), Trichoderma harzianum T-39 (TRICHODEX®, Mycontrol Ltd., Israel; TRICHODERMA 2000®, Makhteshim Ltd., Israel), Trichoderma harzianum ICC012 and Trichoderma viride TRICHOPEL (Agrimm Technologies Ltd, New Zealand), Trichoderma harzianum ICC012 and Trichoderma viride ICC080 (REMEDIER® WP, Isagro Ricerca, Italy), Trichoderma polysporum and Trichoderma harzianum (BINAB®, BINAB Bio-Innovation AB, Sweden), Trichoderma stromaticum TRICOVAB® (C.E.P.L.A.C., Brazil), Trichoderma virens GL-21 (SOILGARD®, Certis LLC, USA), Trichoderma virens G1-3, ATCC 57678, Trichoderma virens G1-21 (Thermo Trilogy Corporation, Wasco, Canada), Trichoderma virens G1-3 and Bacillus amyloliquefaciens FZB2, Trichoderma virens G1-3 and Bacillus· Bacillus amyloliquefaciens NRRL B-50349, Trichoderma virens G1-3, and Bacillus amyloliquefaciens TJ1000, Trichoderma virens G1-21, and Bacillus amyloliquefaciens FZB24, Trichoderma virens G1-21, and Bacillus amyloliquefaciens NRRL B-50349, Trichoderma virens G1-21, and Bacillus amyloliquefaciens TJ1000, Trichoderma viride TRIECO® (Ecosense Labs. (India) Pvt. Ltd., India, BIO-CURE® F, T. Stanes & Co. Ltd., India), Trichoderma viride TV1 (Agribiotec srl, Italy), Trichoderma viride ICC080, and / or Ulocladium oudemansii HRU3 (BOTRY-ZEN®, Botry-Zen Ltd, New Zealand)), and extracts of media comprising these combinations may be included.

[0170] According to some embodiments, the compounds and compositions of the invention may be combined with one or more lipochitooligosaccharides (LCOs), chito-oligosaccharides (COs), and / or chitinaceous compounds. LCOs, also sometimes referred to as common symbiotic nodulation (Nod) signals (or nod factors) or Myc factors, consist of an oligosaccharide backbone of β-1,4-linked N-acetyl-D-glucosamine (“GlcNAc”) residues with N-linked fatty acyl chains condensed at the non-reducing terminus. As is understood in the art, LCOs differ in the number of GlcNAc residues in the backbone, the length and degree of saturation of the fatty acyl chains, and the substitution of reducing or non-reducing sugar residues. See, for example, Denarie et al., Ann. Rev. Biochem. 65:503 (1996); Diaz et al., Mol. Plant-Microbe Interactions 13:268 (2000); Hungria et al., Soil Biol. Biochem. 29:819 (1997); Hamel et al., Planta 232:787 (2010); and Prome et al., Pure&Appl. Chem. 70(1):55 (1998).

[0171] LCO (and its derivatives) may be included or utilized in various purity forms and can be used alone or in the form of a culture broth of LCO-producing bacteria or fungi. For example, OPTIMIZE® (commercially available from Bayer) contains a culture broth of Bradyrhizobium japonicum that produces LCO. Methods for providing substantially pure LCO include removing bacterial cells from a mixture of LCO and microorganisms, or continuing the isolation and purification of LCO molecules by, for example, LCO solvent phase separation as described in U.S. Patent No. 5,549,718, followed by HPLC chromatography. Purification can be facilitated by repeating HPLC chromatography, and the purified LCO molecules can be lyophilized for long-term storage. The compositions and methods of the present disclosure may include LCO analogs, derivatives, hydrates, isomers, circles, and / or solvates. LCO can be incorporated into the compositions according to the invention to any appropriate amount / concentration. For example, the compositions according to the invention comprise from about 1×10 -20 M to about 1×10 -1 M of LCO. The amount / concentration of LCO can be an amount effective to confer favorable traits or benefits to plants, such as enhancing the growth and / or yield of plants to which the composition is applied. According to some embodiments, the LCO amount / concentration is not effective to enhance plant yield without the beneficial contribution from one or more other components of the composition, such as CO and / or one or more pesticides.

[0172] The compounds and compositions of the present invention may be combined, perhaps, with one or more LCOs and with any appropriate CO. COs differ from LCOs in that they do not have the fatty acid pendant molecular chains that are characteristic of LCOs. COs are called N-acetylchitooligosaccharides and consist of GlcNAc residues, but chitin molecules [(C 8 H 13 NO 5 ) n , CAS No. 1398-61-4] and chitosan molecules [(C 5 H 11 NO 4 )nIt has a side chain modification that is different from [CAS No. 9012-76-4]. For example, see D’Haeze et al., Glycobiol. 12(6):79R (2002); Demont-Caulet et al., Plant Physiol. 120(1):83 (1999); Hanel et al., Planta 232:787 (2010); Muller et al., Plant Physiol. 124:733 (2000); Robina et al., Tetrahedron 58:521-530 (2002); Rouge et al., Docking of Chitin Oligomers and Nod Factors on Lectin Domains of the LysM-RLK Receptors in the Medicago-Rhizobium Symbiosis, in The Molecular Immunology of Complex Carbohydrates-3 (Springer Science, 2011); Van der Holst et al., Curr. Opin. Struc. Biol. 11:608 (2001); and Wan et al., Plant Cell 21:1053 (2009). CO may be obtained from any suitable source. For example, CO may be derived from LCO. For example, in an embodiment, the composition according to the invention comprises one or more COs derived from LCO (i.e., isolated and / or purified) obtained from Azorhizobium, Bradyrhizobium (e.g., B. japonicum), Mesorhizobium, Rhizobium (e.g., R. leguminosarum), Sinorhizobium (e.g., S. meliloti), or mycorrhizal fungi (e.g., Glomus intraradicus). Alternatively, CO may be synthesized. Methods for preparing recombinant CO are known in the art.See, for example, Cottaz et al., Meth. Eng. 7(4):311 (2005); Samain et al., Carbohydrate Res. 302:35 (1997.); and Samain et al., J. Biotechnol. 72:33 (1999). These contents and disclosures are incorporated herein by reference.

[0173] CO (and its derivatives) may be included or utilized in various purity forms and can be used alone or in the form of a culture broth of CO-producing bacteria or fungi. It should be understood that the compounds and compositions of the present invention may be combined with hydrates, isomers, salts and / or solvates of CO. CO may be used in any suitable amount / concentration. For example, the composition according to the present invention may comprise from about 1×10 -20 M to about 1×10 -1 M of CO. The amount / concentration of CO can be an amount effective to confer or provide favorable traits or benefits to plants, such as for enhancing the soil microbial environment, enhancing nutrient uptake, or increasing the growth and / or yield of plants to which the composition is applied. According to some embodiments, the CO amount / concentration may not be effective to enhance plant growth without the beneficial contribution from one or more other components of the composition, such as LCO and / or one or more inoculants, biomolecules, nutrients, or pesticides.

[0174] The compounds and compositions of the present invention may be combined with one or more suitable chitinous compounds such as, for example, chitin, chitosan, and their isomers, salts and solvates. Chitin and chitosan, which are the main components of fungal cell walls and the exoskeletons of insects and crustaceans, consist of GlcNAc. Chitin and chitosan may be obtained commercially or prepared from insects, crustacean shells, or fungal cell walls. Methods for preparing chitin and chitosan are known in the art. See, for example, U.S. Patent Nos. 4,536,207 (prepared from crustacean shells) and 5,965,545 (prepared from crab shells and hydrolysis of commercially available chitosan); and Pochanavanich et al., Lett. Appl. Microbiol. 35:17 (2002) (prepared from fungal cell walls). Deacetylated chitin and chitosan in the range of less than 35% to greater than 90% deacetylation and covering a wide spectrum of molecular weights, such as low molecular weight chitosan oligomers of less than 15 kD and chitin oligomers of 0.5 - 2 kD; "practical grade" chitosan of approximately 15 kD molecular weight; and high molecular weight chitosan of 70 kD or less may be obtained. Chitin and chitosan compositions formulated for the intended treatment are commercially available. Commercially available products include, for example, ELEXA® (Plant Defense Boosters, Inc.) and BEYOND™ (Agrihouse, Inc.).

[0175] The compounds and compositions of the present invention may be combined with one or more suitable flavonoids, including, but not limited to, anthocyanidins, anthoxanthins, chalcones, coumarins, flavonones, flavanonols, flavans and isoflavonoids, as well as their analogs, derivatives, hydrates, isomers, polymers, salts and solvates. Flavonoids are phenolic compounds having a general structure of two aromatic rings connected by a three-carbon bridge. The classification of flavonoids is known in the art. See, for example, Jain et al., J. Plant Biochem.&Biotechnol. 11:1 (2002); and Shaw et al., Environ. Microbiol. 11:1867 (2006). This content and disclosure are incorporated herein by reference. Some flavonoid compounds are commercially available. Flavonoid compounds may be isolated from plants or seeds, for example, as described in U.S. Patent Nos. 5,702,752; 5,990,291; and 6,146,668. Flavonoid compounds may also be produced by organisms such as genetically engineered yeast. See, for example, Ralston et al., Plant Physiol. 137:1375 (2005).

[0176] According to some embodiments, the compounds and compositions of the present invention are combined with one or more flavanones such as butin, eriodyctiol, hesperetin, hesperidin, homoeriodyctiol, isosakuranetin, naringenin, narirutin, pinocembryin, poncirin, sakuranetin, sakuranin, and / or one or more of sterubin, one or more flavanonols such as dihydroquercetin and / or taxifolin, one or more flavan-3-ols (e.g., catechin (C), catechin 3-gallate (Cg), epicatechins (EC), epigallocatechin (EGC), epicatechin 3-gallate (ECg), epigallocatechin 3-gallate (EGCg), epiafzelechin, fisetinidol, gallocatechin (GC), gallocatechin 3-gallate (GCg), guibourtinidol, mesquitol, robinetinidol, theaflavin-3-gallate, theaflavin-3'-gallate, theafralavin-3,3'-gallate, thearubigin), flavan-4-ols (e.g., apiforol and / or luteoforol) and / or flavan-3,4-diols (e.g., leucocyanidin, leucodelphinidin, leucofisetinidin, leucomalvidin, leucopelargonidin, leucopeonidin, leucorobinetinidin, melacacidin and / or teracacidin) and / or one or more flavans such as their dimers, trimers, oligomers and / or polymers (e.g., one or more proanthocyanidins), one or more isoflavones or flavonoid derivatives (e.g., biocanin A, daidzein, formononetin, genistein and / or glycitein), isoflavans (e.g., equol, ioncocalpan and / or laxiflorol), isoflavandiols, isoflavens (e.g., grabrine, haginin D and / or 2-methoxydaidzin), coumarins (e.g., coumestrol, pricatin and / or wedelolactone), pterocarpans, rotenoids, neoflavonoids (e.g., calophyllolide, coutareagenin, dalbergichromene, dalbergin, nidulin), and / or pterocarpans (e.g., bavachin A, bavachin B, erybraedin A, erybraedin B, erythrabyssin II, erythrabysin-1, erycristagalin, glycinol, glyceolin, glyceolin, glycyrrhizol, maackiain, medicarpin, molycianin, orientanol, phaseolin, pisatin, striatin, trifolirhizin) and one or more isoflavonoids such as these, and may be combined in combination with these. Flavonoids and their derivatives may be included in the composition in any suitable form, including but not limited to polymorphic and crystalline forms. Flavonoids may be included in the composition according to the invention in any suitable amount or concentration. The amount / concentration of flavonoids may be an amount effective to confer a benefit to the plant and may act directly on soil microorganisms or other means, such as to enhance phytohormones and / or yield. According to some embodiments, the amount / concentration of flavonoids may not be effective to enhance the plant's nutrients or yield without the beneficial contribution from one or more other components of the composition, such as LCO, CO and / or one or more pesticides.

[0177] The compounds and compositions of the present invention may be combined with one or more suitable non-flavonoid nod gene inducers, examples of which include jasmonic acid ([1R-[1α,2β(Z)]]-3-oxo-2-(pentenyl)cyclopentaneacetic acid; JA), linoleic acid ((Z,Z)-9,12-octadecadienoic acid) and / or linolenic acid ((Z,Z,Z)-9,12,15-octadecatrienoic acid), and their analogs, derivatives, hydrates, isomers, polymers, salts and solvates, but are not limited thereto. Jasmonic acid and its methyl ester, methyl jasmonate (MeJA), which are collectively known as jasmonic acid esters, are octadecanoid-based compounds that occur naturally in some plants (e.g., wheat), fungi (e.g., Botryodiplodia theobromae, Gibbrella fujikuroi), enzymes (e.g., Saccharomyces cerevisiae) and bacteria (e.g., Escherichia coli). Linoleic acid and linolenic acid may be produced during the biosynthesis of jasmonic acid. Jasmonic acid esters, linoleic acid and linolenic acid (and their derivatives) have been reported to be inducers of nod gene expression or LCO production by rhizosphere bacteria. See, for example, Mabood et al., Plant Physiol. Biochem. 44(11):759 (2006); Mabood et al., Agr. J. 98(2):289 (2006); Mabood et al., Field Crops Res. 95(2-3):412 (2006); and Mabood&Smith, Linoleic and linolenic acid induce the expression of nod genes in Bradyrhizobium japonicum USDA 3, Plant Biol. (2001).

[0178] Derivatives of jasmonic acid, linoleic acid, and linolenic acid that can be contained or used in combination with the compounds and compositions according to the present invention include esters, amides, glycosides, and salts thereof. Representative esters are compounds in which the carboxyl group of linoleic acid, linolenic acid, or jasmonic acid is substituted by a -COR group, where R of the -COR group is R 1 is: C 1 ~C 8 a non-branched or branched alkyl group, for example, an alkyl group such as a methyl, ethyl, or propyl group; C 2 ~C 8 an alkenyl group such as a non-branched or branched alkenyl group; C 2 ~C 8 an alkynyl group such as a non-branched or branched alkynyl group; for example, an aryl group having 6 to 10 carbon atoms; or a heteroaryl group having, for example, 4 to 9 carbon atoms, where the heteroatom in the heteroaryl group can be, for example, N, O, P, or S, -OR 1 is. Representative amides are compounds in which the carboxyl group of linoleic acid, linolenic acid, or jasmonic acid is substituted by a -COR group, where R of the -COR group is R 2 and R 3 are each independently: hydrogen; C 1 ~C 8 a non-branched or branched alkyl group, for example, an alkyl group such as a methyl, ethyl, or propyl group; C 2 ~C 8 an alkenyl group such as a non-branched or branched alkenyl group; C 2 ~C 8 an alkynyl group such as a non-branched or branched alkynyl group; for example, an aryl group having 6 to 10 carbon atoms; or a heteroaryl group having, for example, 4 to 9 carbon atoms, where the heteroatom in the heteroaryl group can be, for example, N, O, P, or S, NR 2 R 3It is a base. The ester may be prepared by a known method such as an acid-catalyzed nucleophilic addition reaction in which a carboxylic acid is reacted with an alcohol in the presence of a catalytic amount of a mineral acid. The amide may be prepared by a known method such as reacting a carboxylic acid with a suitable amine in the presence of a coupling agent such as dicyclohexylcarbodiimide (DCC) under neutral conditions. Suitable salts of linoleic acid, linolenic acid, and jasmonic acid include, for example, base addition salts. Bases that may be used as reagents for preparing metabolically acceptable base salts of these compounds include those derived from cations such as alkali metal cations (e.g., potassium and sodium) and alkaline earth metal cations (e.g., calcium and magnesium). These salts can be easily prepared by mixing a solution of linoleic acid, linolenic acid, or jasmonic acid with a solution of the base. The salt may be precipitated from the solution and collected by filtration, or recovered by other means such as evaporation of the solvent.

[0179] The non-flavonoid nod gene inducer may be used in combination with the compounds and compositions of the present invention in any suitable amount / concentration. For example, the amount / concentration of the non-flavonoid nod gene inducer may be an amount effective to confer or provide a preferred trait or benefit to the plant, such as enhancing the growth and / or yield of the plant to which the composition is applied. According to some embodiments, the amount / concentration of the non-flavonoid nod gene inducer may not be effective to enhance the growth and / or yield of the plant without a beneficial contribution from one or more other components of the composition, such as LCO, CO, and / or one or more pesticides.

[0180] The compounds and compositions of the present invention may be combined well with carotenoids, including but not limited to 2H-furo[2,3-c]pyran-2-one, and their analogs, derivatives, hydrates, isomers, polymers, salts and solvates. Examples of biologically acceptable salts of carotenoids include acid addition salts formed with biologically acceptable acids, such as hydrochloric acid, hydrobromic acid, sulfate or bisulfate, phosphate or hydrogen phosphate, acetate, benzoate, succinate, fumarate, maleate, lactate, citrate, tartrate, gluconate; methanesulfonate, benzenesulfonate and p-toluenesulfonic acid. Further biologically acceptable metal salts can include alkali metal salts with bases, such as sodium salts and potassium salts. Carotenoids can be incorporated into the compositions according to the present invention in any suitable amount or concentration. For example, the amount / concentration of carotenoids can be an amount effective to confer or provide favorable traits or benefits to plants, such as enhancing the growth and / or yield of plants on which the composition is sprayed. In an embodiment, the amount / concentration of carotenoids may not be effective to enhance plant nutrients and / or yield without the beneficial contribution from one or more other components of the composition, such as LCO, CO and / or one or more pesticides.

[0181] The compounds and compositions of the present invention may be combined with one or more anthocyanidins and / or anthoxanthins, such as cyanidin, delphinidin, malvidin, pelargonidin, peonidin, petunidin, flavones (e.g., apigenin, baicalein, chrysin, 7,8-dihydroxyflavone, diosmin, flavoxate, 6-hydroxyflavone, luteolin, scutellarein, tangeretin, and / or wogonin) and / or flavonols (e.g., amrencin, astragalin, azaleatin, azalein, fisetin, furanoflavonol galangin, gossypetin, 3-hydroxyflavone, hyperoside, icariin, isokercetin, kaempferid, kaempferitrin, kaempferol, isolamnetin, morin, myricetin, myricitrin, natsudaidain, pakipodol, pyranoflavonol quercetin, quercetin, rhamnazin, rhamnetin, robinin, rutin, spireoside, troxerutin, and / or xanthramnin, and combinations of one or more thereof).

[0182] The compounds and compositions of the present invention may be combined with gluconolactone and / or their analogs, derivatives, hydrates, isomers, polymers, salts, and / or solvates. Gluconolactone can be incorporated into the compositions according to the present invention to any suitable amount / concentration. For example, the amount / concentration of gluconolactone can be an effective amount to confer or provide favorable traits or benefits to plants, such as enhancing the growth and / or yield of plants to which the composition is applied. In an aspect, the amount / concentration of gluconolactone may not be effective to enhance the nutrient and / or yield of plants without the beneficial contribution from one or more other components of the composition, such as LCO, CO, and / or one or more insecticides.

[0183] The compounds and compositions of the present invention are combined with organic acids (e.g., acetic acid, citric acid, lactic acid, malic acid, taurine, etc.), major minerals (e.g., phosphorus, calcium, magnesium, potassium, sodium, iron, etc.), trace minerals (e.g., boron, cobalt, chloride, chromium, copper, fluoride, iodide, iron, manganese, molybdenum, selenium, zinc, etc.), vitamins (e.g., vitamin A, vitamin B group (i.e., vitamin B 1 ), vitamin B 2 ), vitamin B 3 ), vitamin B 5 ), vitamin B 6 ), vitamin B 7 ), vitamin B 8 ), vitamin B 9 ), vitamin B 12、choline), vitamin C, vitamin D, vitamin E, vitamin K), and / or carotenoids (α-carotene, β-carotene, cryptoxanthin, lutein, lycopene, zeaxanthin, others), and may be combined with one or more suitable nutrients and / or fertilizers such as combinations thereof. In some embodiments, the compounds and compositions of the present invention may be combined with the macronutrients and micronutrients of plants or microorganisms including phosphorus, boron, choline, copper, iron, manganese, molybdenum and / or zinc. According to some embodiments, the compounds and compositions of the present invention may be combined with one or more beneficial micronutrients. Non-limiting examples of micronutrients for use in the compositions described herein include vitamins (vitamin A, vitamin B group (i.e., vitamin B1, vitamin B2, vitamin B3, vitamin B5, vitamin B6, vitamin B7, vitamin B8, vitamin B9, vitamin B12, choline), vitamin C, vitamin D, vitamin E, vitamin K), carotenoids (α-carotene, β-carotene, cryptoxanthin, lutein, lycopene, zeaxanthin, others), major minerals (e.g., phosphorus, calcium, magnesium, potassium, sodium, iron, others), trace minerals (e.g., boron, cobalt, chloride, chromium, copper, fluoride, iodide, iron, manganese, molybdenum, selenium, zinc, others), organic acids (e.g., acetic acid, citric acid, lactic acid, malic acid, tartaric acid, others), and combinations thereof (BAYFOLAN secure, BAYFOLAN complete, BAYFOLAN energy, BAYFOLAN power, Aglukon GmbH, Germany). In certain embodiments, the composition may comprise phosphorus, boron, chlorine, copper, iron, manganese, molybdenum, and / or zinc, and combinations thereof. For compositions comprising phosphorus, it is contemplated that any suitable source of phosphorus may be used.For example, phosphorus can be from a phosphate ore source such as monoammonium phosphate, diammonium phosphate, monocalcium phosphate, superphosphate, triple superphosphate, and / or ammonium polyphosphate, an organic phosphorus source that can be solubilized by one or more microorganisms (e.g., Penicillium bilaiae), or a phosphorus source derivative.

[0184] Formulation In a further embodiment, the present invention relates to a plant protection agent in the form of a conventional formulation comprising polymorphic form B of (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine of formula (I).

[0185] In a preferred embodiment of the present invention, the plant protection agent comprises more than 90% by weight, preferably more than 95% by weight, of polymorphic form B of the compound of formula (I) based on the total amount of all forms of the compound of formula (I) present in the composition.

[0186] In a more preferred embodiment, the present invention relates to a suspension concentrate (SC) formulation comprising polymorphic form B of the compound of formula (I), one or more dispersants, one or more defoamers, one or more biocides, one or more rheology additives, one or more antifreezes and / or one or more carriers.

[0187] In a further embodiment, the present invention relates to the use of a pesticidal formulation comprising polymorphic form B of the compound of formula (I) for foliar spraying, for these uses in low-volume spraying, for unmanned aerial systems (UAS), unmanned ground vehicles (UGV), and tractor-mounted boom sprayers equipped with conventional nozzles, as well as for pulse-width modulation spray nozzles or rotary disk spray particle spreaders, and for controlling diseases related to agriculture, particularly with respect to the spraying of these on waxy leaves. Specifically, the present invention relates to a pesticidal composition with reduced drift, particularly in spray applications.

[0188] In one aspect, the present invention is: a) Polymorphic form B of the compound of formula (I) and one or more further active ingredients such as fungicides, antibacterial agents, acaricides, nematicides, insecticides, biocontrol agents or herbicides, b) one or more drift-reducing agents, c) one or more spreading agents, d) one or more uptake promoters, e) one or more rainfastness additives, f) other formulation ingredients (formulants), g) a carrier up to a predetermined volume (1 L or 1 kg), relating to a formulation comprising.

[0189] In one preferred embodiment, b) is a vegetable oil or a vegetable oil ester or diester, and in another embodiment, b) is a polymeric drift-reducing agent.

[0190] Drift-reducing agent b) Suitable drift-reducing agents are poly(ethylene oxide), said polymer preferably having an average molecular weight of 0.5 to 12 million g / mol, more preferably 0.75 to 10 million g / mol, most preferably 1 to 8 million g / mol, and hydroxypropyl guar, as well as vegetable oils and vegetable oil esters and diesters (including esters containing glycerin and propylene glycol).

[0191] Particularly preferred are methyl, ethyl, isopropyl, isobutyl, butyl, hexyl and ethylhexyl esters.

[0192] More preferably, the vegetable oil and ester are selected from the group consisting of methyl oleate, methyl palmitate, rapeseed oil methyl ester, isopropyl myristate, isopropyl palmitate, ethylhexyl palmitate, ethylhexyl oleate, ethylhexyl palmitate / ethylhexyl laurate mixture, ethylhexyl laurate, ethylhexyl caprylate / ethylhexyl caprate mixture, diisopropyl adipate, coconut oil propylene glycol diester, sunflower oil, rapeseed oil, corn oil, soybean oil, rice oil, olive oil, peanut oil, mixed caprylic and capric triglycerides, and mixed decanoyl and octanoyl glycerides.

[0193] Furthermore, suitable as the drift reducer is mineral oil.

[0194] Spreader c) Suitable spreaders are selected from the group consisting of mono- and diesters of metal sulfosuccinates with branched or straight-chain alcohols containing 1 to 10 carbon atoms, especially alkali metal salts, more especially sodium salts, most especially sodium dioctyl sulfosuccinate; and organic silicone ethoxylates such as organic modified polysiloxanes / trisiloxane alkoxylates including the following CAS No. 27306-78-1, 67674-67-3, 134180-76-0, for example, Silwet® L77, Silwet® 408, Silwet® 806, BreakThru® S240, BreakThru® S278.

[0195] Other suitable spreaders are ethoxylated diacetylene-diols with 1 to 6 EO, for example, Surfynol® 420 and 440, and 1-hexanol, 3,5,5-trimethyl-, ethoxylated, propoxylated (CAS-No. 204336-40-3), for example, Break-Thru® Vibrant.

[0196] Preferred are those selected from the group consisting of polyalkylene oxide-modified heptamethyltrisiloxane; more preferably, siloxane group poly(oxy-1,2-ethanediyl), α-methyl-ω-[3-[1,3,3,3-tetramethyl-1-[(trimethylsilyl)oxy]disiloxanyl]propoxy] (CAS-No. 27306-78-1); poly(oxy-1,2-ethanediyl), α-[3-[1,3,3,3-tetramethyl-1-[(trimethylsilyl)oxy]disiloxanyl]propyl]-ω-hydroxy (CAS-No. 67674-67-3); and the polymer of oxirane, methyl-, with oxirane, mono 3-1,3,3,3-tetramethyl-1-(trimethylsilyl)oxydisiloxanylpropyl ether (CAS-No. 134180-76-0).

[0197] Preferably, the spreading agent is selected from the group consisting of sodium dioctyl sulfosuccinate, polyalkylene oxide-modified heptamethyltrisiloxane, and ethoxylated diacetylene-diols.

[0198] Uptake promoter d) The uptake promoter may be selected from the group of the following compounds: Other suitable uptake promoters are alcohol ethoxylates selected from the group consisting of ethoxylated alcohols, propoxy-ethoxylated alcohols, ethoxylated carboxylic acids, propoxy-ethoxylated carboxylic acids, or ethoxylated mono-, di- or triesters of glycerin comprising fatty acids having 8 to 18 carbon atoms and an average of 5 to 40 EO units. The ethoxylated or propoxy-ethoxylated alcohol or carboxylic acid may be further modified by addition of methyl radicals to the remaining alcohol functional groups ("Me end-capping"). The term "alcohol" as described in d) represents an alcohol having 6 to 22 carbon atoms, which may be branched or straight-chain, saturated or unsaturated, and may have further substituents such as an OH group. The term "carboxylic acid" as described in d) represents a carboxylic acid having 6 to 22 carbon atoms, which may be branched or straight-chain, saturated or unsaturated, and may have further substituents such as an OH group.

[0199] As an example, suitable components as described in d) are as follows: - Ethoxylated linear and / or branched fatty alcohols containing 2 to 20 EO units (e.g., type X of Genapol® Clariant); - Methyl end-capped, ethoxylated linear and / or branched fatty alcohols containing 2 to 20 EO units (e.g., type XM of Genapol® Clariant); - Ethoxylated coconut alcohol containing 2 to 20 EO units (e.g., type C of Genapol® Clariant): - Ethoxylated C12 / 15 alcohol containing 2 to 20 EO units (e.g., type A of Synperonic® Croda); - Propoxy-ethoxylated alcohols, branched and / or linear, e.g., B / 848 of Antarox® Solvay, G5000 of Atlas® Croda, HOT 5902 of Lucramul® Levaco; -Propoxy-ethoxylated fatty acids, Me-end capped, e.g., OC0503M of Leofat® Lion; -Alkyl ether citrate surfactants (e.g., Adsee CE line-up, Akzo Nobel); -Alkyl polysaccharides (e.g., Agnique® PG8107, PG8105 of BASF; Atplus® 438, AL-2559, AL-2575 of Croda); -Ethoxylated mono- or diesters of glycerin comprising fatty acids having 8 to 18 carbon atoms and an average of 10 to 40 EO units (e.g., product line-up of Crovol® Croda); -Castor oil ethoxylates comprising an average of 5 to 40 EO units (e.g., Berol® line-up of Nouryon, Emulsogen® EL line-up of Clariant); -Ethoxylated oleic acid comprising 2 to 20 EO units (e.g., Alkamuls® A and AP); -Ethoxylated sorbitan fatty acid esters comprising fatty acids having 8 to 18 carbon atoms and an average of 10 to 50 EO units (e.g., Arlatone® T, Tween line-up).

[0200] Weather resistance additive e) Suitable weather resistance additives are acrylic-based emulsion polymers or polymer dispersants. Styrene-based emulsion polymers or polymer dispersants d) are aqueous polymer dispersants having a Tg in the range of -100 °C to 30 °C, preferably -60 °C to 20 °C, more preferably -50 °C to 10 °C, and most preferably -45 °C to 5 °C, e.g., Acronal V215, Acronal 3612, Licomer ADH 205, and Atplus FA. Particularly preferred are Licomer ADH205 and Atplus FA.

[0201] Preferably, the polymer is selected from the group consisting of acrylic polymers, styrene polymers, vinyl polymers and their derivatives, polyolefins, polyurethanes and natural polymers and their derivatives.

[0202] More preferably, the polymer is selected from the group consisting of acrylic polymers, styrene-butadiene copolymers, styrene-maleic anhydride copolymers, polyvinyl alcohol, polyvinyl acetate, partially hydrolyzed polyvinyl acetate, methyl vinyl ether-maleic anhydride copolymers, carboxy-modified polyvinyl alcohol, acetoacetyl-modified polyvinyl alcohol, diacetone-modified polyvinyl alcohol and silicon-modified polyvinyl alcohol, isopropylene-maleic anhydride copolymers, polyurethanes, cellulose, gelatin, caesin, oxidized starch, starch-vinyl acetate graft copolymers, hydroxyethyl cellulose, methyl cellulose, ethyl cellulose, carboxymethyl cellulose and acetyl cellulose.

[0203] Most preferably, the polymer is selected from copolymers of acrylates and styrenes. The acrylate is selected from the list consisting of 2-ethylhexyl acrylate, butyl acrylate, sec-butyl acrylate, ethyl acrylate, methyl acrylate, acrylic acid, acrylamide, iso-butyl acrylate, methyl methacrylate, or combinations thereof. The styrenes are selected from the list consisting of styrene, tert-butyl styrene, para-methyl styrene, or combinations thereof.

[0204] In a preferred embodiment, the polymer has a molecular weight of 40,000 or less, preferably 10,000 or less.

[0205] In a preferred embodiment, the polymer D is the emulsion polymer described in International Publication No. WO 2017 / 202684.

[0206] The glass transition temperature (Tg) is known for many polymers and, unless otherwise specified, is determined in the present invention in accordance with ASTM E1356-08 (2014) “Standard Test Method for Assignment of the Glass Transition Temperatures by Differential Scanning Calorimetry”. The sample is dried at 110 °C for 1 hour before DSC to eliminate the influence of water and / or solvents. The DSC sample size is 10-15 mg, and the measurement is carried out from -100 °C to 100 °C at 20 °C / min under N2. Tg is defined as the midpoint of the transition region.

[0207] Other formulations f) f1 Suitable non-ionic surfactants or dispersion aids f1) are all substances of this type that can be customarily used in pesticides. Preferably, they have a molecular weight of more than 6,000 g / mol or a polyethylene oxide content of more than 45%. More preferably, they are polyethylene oxide-polypropylene oxide block copolymers, polyoxyalkylene amine derivatives, polyvinylpyrrolidone, copolymers of polyvinyl alcohol and polyvinylpyrrolidone, and copolymers of (meth)acrylic acid and (meth)acrylic acid esters, which have a molecular weight of more than 6,000 g / mol and a polyethylene oxide content of more than 45%. Among the above examples, the selected classification can be phosphorylated, sulfonated or sulfated and neutralized with a base as needed.

[0208] Possible anionic surfactants or dispersing aids f1) are all substances of this type that can be customarily used in pesticides. Alkali metal, alkaline earth metal, and ammonium salts of alkyl sulfonic acids or alkyl phosphoric acids and alkyl aryl sulfonic acids or alkyl aryl phosphoric acids are preferred. A more preferred group of anionic surfactants or dispersing aids are the alkali metal, alkaline earth metal, and ammonium salts of polystyrene sulfonic acid, salts of polyvinyl sulfonic acid, salts of alkyl naphthalene sulfonic acid, salts of naphthalene sulfonic acid-formaldehyde condensation products, salts of condensation products of naphthalene sulfonic acid, phenol sulfonic acid, and formaldehyde, and salts of lignosulfonic acid.

[0209] f2 Rheology modifiers are additives that, when added to the recipe at a concentration that reduces the gravitational separation of the dispersed active ingredient during storage, result in a substantial increase in viscosity at low shear rates. Low shear rates are defined as follows and, for the purposes of the present invention, a substantial increase is defined as more than double. Viscosity can be measured using a rotational shear rheometer. -1 as follows, and for the purposes of the present invention, a substantial increase is defined as more than double. Viscosity can be measured using a rotational shear rheometer.

[0210] As an example, suitable rheology modifiers E2) are as follows: - Polysaccharides containing xanthan gum, and hydroxyethyl cellulose. Examples are Kelzan®, Rhodopol® G and 23, Satiaxane® CX911 and Natrosol® 250 lineup. - Clays containing montmorillonite, bentonite, sepiolite, attapulgite, laponite, hectorite. Examples are Veegum® R, Van Gel® B, Bentone® 34, 38, CT, HC, EW, Pangel® M100, M200, M300, S, M, W, Attagel® 50, Laponite® RD. - Fumed silica and precipitated silica, examples are Aerosil® 200, Sipernat® 22.

[0211] Preferred are xanthan gum, montmorillonite clay, bentonite clay and fumed silica.

[0212] f3 Suitable defoaming substances (e3) are all substances that can customarily be used in pesticides for this purpose. Silicone oils and silicone oil formulations are preferred. Examples are Silcolapse® 426 and 432 from Bluestar Silicones, Silfoam® SRE and SC132 from Wacker, SAF-184® from Silchem, Foam-Clear ArraPro-S® from Basildon Chemical Company Ltd, SAG® 1572 and SAG® 30 [dimethyl siloxanes and silicones, CAS No. 63148-62-9] from Momentive. Preferred is SAG® 1572.

[0213] f4 Suitable antifreezing agents are all substances that can customarily be used in pesticides for this purpose. Suitable examples are propylene glycol, ethylene glycol, urea and glycerin.

[0214] f5 Suitable other formulation components (e5) are selected from biocides, colorants, pH adjusters, buffers, stabilizers, antioxidants, inert fillers, humectants, crystal growth inhibitors, micronutrients, and as an example, the following are:

[0215] Possible preservatives are all substances that can customarily be used in pesticides for this purpose. Suitable examples of preservatives are preparations containing 5-chloro-2-methyl-4-isothiazolin-3-one [CAS-No. 26172-55-4], 2-methyl-4-isothiazolin-3-one [CAS-No. 2682-20-4] or 1,2-benzisothiazol-3(2H)-one [CAS-No. 2634-33-5]. Examples that may be mentioned are Preventol® D7 (Lanxess), Kathon® CG / ICP (Dow), Acticide® SPX (Thor GmbH) and Proxel® GXL (Arch Chemicals).

[0216] Possible colorants are all substances that can customarily be used in pesticides for this purpose. Titanium dioxide, carbon black, zinc oxide, blue pigments, brilliant blue FCF, red pigments and permanent red FGR may be mentioned as an example.

[0217] Possible pH regulators and buffers are all substances that can customarily be used in pesticides for this purpose. Citric acid, sulfuric acid, hydrochloric acid, sodium hydroxide, sodium hydrogen phosphate (Na 2 HPO 4 ), sodium dihydrogen phosphate (NaH 2 PO 4 ), potassium dihydrogen phosphate (KH 2 PO 4 ), potassium hydrogen phosphate (K 2 HPO 4 ) may be mentioned as an example.

[0218] Suitable stabilizers and antioxidants are all substances that can customarily be used in pesticides for this purpose. Butylhydroxytoluene [3,5-di-tert-butyl-4-hydroxytoluene, CAS-No. 128-37-0] is preferred.

[0219] The carrier can be one that is customarily used for this purpose in agrochemical formulations.

[0220] The carrier is generally inert and is a solid or liquid, natural or synthetic, organic or inorganic substance that can be used as a solvent. The carrier generally improves the application of the compound to, for example, plants, plant parts, or seeds.

[0221] Examples of suitable solid carriers include ammonium salts, especially ammonium sulfate, ammonium phosphate, and ammonium nitrate, natural rock powders such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite, and diatomaceous earth, silica gels such as microsilica, alumina, silicates, and synthetic rock powders, but are not limited thereto. Examples of typically useful solid carriers for preparing granules include ground and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite, synthetic granules of inorganic and organic wheat flours, and granules of organic materials such as paper, sawdust, coconut shells, corn cobs, and tobacco stems, but are not limited thereto.

[0222] Preferred solid carriers are selected from clay, talc, and silica.

[0223] Examples of suitable liquid carriers include, but are not limited to, water, organic solvents, and combinations thereof. Examples of suitable solvents include, for example, polar and nonpolar organic chemical liquids from the following classifications: - Alcohols and polyols (ethanol, propanol, butanol, benzyl alcohol, cyclohexanol or glycols, 2-ethylhexanol, etc., which may be substituted, etherified and / or esterified), - Dioctyl ether, tetrahydrofuran, dimethyl isosorbide, solketal, cyclopentyl methyl ether, solvents provided by Dow under the Dowanol Product Range, such as Dowanol DPM, anisole, phenetole, different molecular weight grades of dimethyl polyethylene glycol, different molecular weight grades of dimethyl polypropylene glycol, ethers such as dibenzyl ether, - Ketones (acetone, methyl ethyl ketone, methyl isobutyl ketone, cyclopentanone, cyclohexanone, cycloheptanone, acetophenone, propiophenone, etc.), - Lactate esters such as methyl lactate, ethyl lactate, propyl lactate, butyl lactate, 2-ethylhexyl lactate, - (Poly)ethers such as different molecular weight grades of polyethylene glycol, different molecular weight grades of polypropylene glycol, - Unsubstituted and substituted amines, - Amides (fatty acid amides such as dimethylformamide, or N,N-dimethyl lactamide, or N-formylmorpholine, or N,N-dimethyldecanamide, or N,N-dimethyldec-9-en-amide, etc.) and their esters, - Lactams (N-alkylpyrrolidones such as 2-pyrrolidone, or N-methylpyrrolidone, or N-butylpyrrolidone, or N-octylpyrrolidone, or N-dodecylpyrrolidone, or N-methylcaprolactam, N-alkylcaprolactam, etc.), - Lactones (γ-butyrolactone, γ-valerolactone, δ-valerolactone, or α-methyl-γ-butyrolactone, etc.), - Sulfones and sulfoxides (such as dimethyl sulfoxide), - Nitriles (linear or cyclic alkyl nitriles, especially acetonitrile, cyclohexanecarbonitrile, octanonitrile, dodecanonitrile, etc.), - Diethyl carbonate, dipropyl carbonate, dibutyl carbonate, dioctyl carbonate, or linear and cyclic carbonates such as ethylene carbonate, propylene carbonate, butylene carbonate, glycerin carbonate.

[0224] The most preferred carrier is water.

[0225] These spraying liquids are dispersed by conventional methods, i.e., for example, spraying, pouring or injection, particularly spraying, most particularly spraying by UAV.

Examples

[0226] A. Methods and Abbreviations A-1. Methods All data that are part of this application were prepared by the following methods, unless otherwise specified. Samples used for measurement were used directly without further sample preparation.

[0227] Measurement of LogP value The measurement of LogP value provided in this specification was performed by HPLC (High Performance Liquid Chromatography) on a reverse-phase column using the method determined by LC-UV measurement in the acidic range using water and 0.1% formic acid in acetonitrile (linear gradient from 10% acetonitrile to 95% acetonitrile) as the eluent, in accordance with EEC directive 79 / 831 Annex V.A8.

[0228] Calibration was performed with linear alkan-2-ones (having 3 to 16 carbon atoms) having known LogP values (measurement of LogP values using retention times by linear interpolation between consecutive alkanones). The maximum lambda value was determined using the UV spectrum from 200 nm to 400 nm and the peak value of the chromatographic signal.

[0229] 1 1H-NMR data of the selected examples provided in this specification 1 1H-NMR data are 1It is described in the form of an H-NMR peak list. For each signal peak, the δ value is listed in ppm, and the signal intensity is shown within parentheses. A semicolon exists as a delimiter between the δ value-signal intensity pairs.

[0230] Therefore, a peak list for an example has the following form. d1(intensity 1); d2(intensity 2); ……..; di(intensity i); …; dn(intensity n)

[0231] The sharp signal intensity correlates with the signal height (cm) in the printed example of the NMR spectrum and indicates the actual relationship of the signal intensities. From a broad signal, the relative intensities of several peaks or the center of the signal compared to the strongest signal in the spectrum can be shown.

[0232] 1 To calibrate the chemical shift of the H spectrum, especially for spectra measured in DMSO, the chemical shift of tetramethylsilane and / or the solvent used is employed. Therefore, in the NMR peak list, the peak of tetramethylsilane may or may not occur.

[0233] 1 The H-NMR peak list is similar to the conventional 1 H-NMR print and thus usually includes all peaks and is listed in the conventional NMR interpretation.

[0234] Furthermore, they can show, like the conventional 1 H-NMR print signals of the solvent, the stereoisomers of the target compound which is also the subject of the present invention, and / or the peaks of impurities.

[0235] To display the compound signal within the δ range of the solvent and / or water, the normal peaks of the solvent, for example, the peak of DMSO in DMSO-D 6 and the peak of water are those of the inventors 1Shown in the H-NMR peak list, generally having a high intensity on average.

[0236] The peaks of the stereoisomers and / or impurities of the target compound generally have a lower intensity than the peaks of the target compound (e.g., purity > 90%) on average.

[0237] Such stereoisomers and / or impurities may be normal for a specific manufacturing method. Therefore, their peaks can help recognize the reproducibility of the preparation process of the present inventors through the "by-product fingerprint".

[0238] Experts who calculate the peaks of the target compound using known methods (also having empirically evaluated expected values, MestreC, ACD simulations) can separate the peaks of the target compound as needed using an additional intensity filter if desired. This separation may be similar to the picking of relevant peaks in conventional 1 H-NMR interpretation.

[0239] Details of the description of NMR data including the peak list are described in the publication "Citation of NMR Peaklist Data within Patent Applications" of the Research Disclosure Database (No. 564025).

[0240] Separation of enantiomers The enantiomeric separation of the racemate was carried out by preparative supercritical fluid chromatography using supercritical carbon dioxide as the mobile phase and a lower alcohol, more preferably methanol, ethanol or isopropanol, in a ratio of 15% to 30% by volume as a modifier. Commercially available, in one of the following known chiral stationary phases with a thermostat, the total flow rate ranges from 70 to 100 ml / min, the chromatographic separation is carried out in the range of 30°C to 50°C, and the back pressure ranges from 70 bar to 130 bar: - ChiralPak (registered trademark) IA from Daicel Chemical Industries, Ltd., 250×20 mm, - Lux (registered trademark) Amylose-1 from Phenomenex Inc., 250×21.2 mm 5μm, Axia packed, - Lux (registered trademark) Cellulose-1 from Phenomenex Inc., 250×21.2 mm 5μm, Axia packed, - Lux (registered trademark) i-Cellulose-5 from Phenomenex Inc., 250×21.2 mm 5μm, Axia packed.

[0241] XRPD The X-ray diffraction pattern was recorded at room temperature using an XRD diffractometer X’Pert PRO (PANalytical) and a STOE STADI-P (irradiation Cu Kα1, wavelength 1.5406 Å). The total X-ray reflection was cited as the °2θ (theta) value (peak maximum) at a resolution of ±0.2°.

[0242] Raman The Raman spectrum was recorded at room temperature using an FT-Raman spectrometer (model MultiRam) from Bruker. The resolution was 2 cm -1 . Measurements were made in a glass vial or an aluminum disk.

[0243] IR IR-ATR was recorded at room temperature using an FT-IR spectrometer Tensor 37 from Bruker or an Alpha equipped with a universal diamond ATR device. The resolution was 2 cm -1 .

[0244] TGA The TGA thermograms were recorded using a thermobalance from Perkin-Elmer (model TGA8000) and one from Mettler Toledo (model TGA / DSC3+). Measurements were carried out at a heating rate of 10 K / min using an open platinum pan (Perkin Elmer) and a perforated aluminum pan (Mettler). The flow gas was nitrogen.

[0245] B. Examples B-1. Preparation by synthesis Preparation of Example 1: (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine (I) [2446130-20-5] Step 1: Preparation of N-[(2RS)-1-chloro-3-(2-chloro-4-methylphenyl)propan-2-yl]-3-(3-chloro-2-fluorophenoxy)-6-methylpyridazine-4-carboxamide [2446133-45-3] Under argon, 3-(3-chloro-2-fluorophenoxy)-6-methylpyridazine-4-carboxylic acid [2435607-79-5] (175 g, 619 mmol) and (2RS)-1-chloro-3-(2-chloro-4-methylphenyl)propan-2-amine hydrochloride (1:1) [2446132-78-9] (262 g, 928 mmol) were suspended in 3 L of dichloromethane, and then propanephosphoric anhydride (682 mL, 2290 mmol) was slowly added over 10 minutes. N,N-Diisopropylethylamine (393 mL, 2250 mmol) was added dropwise, and the reaction mixture was stirred at room temperature for 18 hours. Then, the reaction mixture was poured into 1.5 L of a saturated aqueous solution of sodium bicarbonate, and 1 L of water was added. The mixture was extracted twice with 500 ml of dichloromethane. The combined organic layers were dried over sodium sulfate, filtered, and evaporated. The product was purified by column chromatography on a 3 kg silica gel column (solid deposition) with an eluent of a heptane / ethyl acetate gradient of 100 / 0 to 0 / 100. After evaporation of the solvent, 250 g of the title compound (purity 100%, yield 83%) was recovered as a solid.

[0246] Process 2: Preparation of N-[(2RS)-1-chloro-3-(2-chloro-4-methylphenyl)propan-2-yl]-3-(3-chloro-2-fluorophenoxy)-N'-hydroxy-6-methylpyridazine-4-carboximidamide [2446133-13-5] To a solution of N-[(2RS)-1-chloro-3-(2-chloro-4-methylphenyl)propan-2-yl]-3-(3-chloro-2-fluorophenoxy)-6-methylpyridazine-4-carboxamide [2446133-45-3] (249 g, 515 mmol) in toluene (3 L) was added phosphorus pentachloride (215 g, 1030 mmol). The reaction mixture was stirred at 75 °C for 1 h and then concentrated under reduced pressure. The residue was dissolved in 1,4-dioxane (1.2 L), and a solution of hydroxylamine (681 g, 10.3 mol, 50% aqueous solution) diluted with 1,4-dioxane (2.8 L) was added to the reaction mixture at 15 °C over 30 min. After stirring at room temperature for 16 h, the reaction mixture was diluted with water (6 L), and then 1.6 L of 6 M hydrochloric acid was added slowly. The aqueous phase was extracted with ethyl acetate (4 × 750 mL). The organic extracts were washed with brine (1 L), dried over sodium sulfate, filtered, and concentrated under reduced pressure. The solvent was evaporated to give 309 g (purity 80%, yield 96%) of the title product as a yellow oil.

[0247] Process 3: Preparation of (5RS)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine [2446129-82-2] To a solution of N-[(2RS)-1-chloro-3-(2-chloro-4-methylphenyl)propan-2-yl]-3-(3-chloro-2-fluorophenoxy)-N’-hydroxy-6-methylpyridazine-4-carboximidamide [2446133-13-5] (278 g, 474 mmol) in acetonitrile (5 L) and water (50 mL) was added potassium tert-butoxide (173 g, 830 mmol). The reaction mixture was stirred at 45 °C for 45 minutes. The reaction mixture was diluted with water (1 L) and the acetonitrile was evaporated under vacuum. The resulting mixture was diluted with water (8 L) and extracted with ethyl acetate (3 × 1.5 L). The combined organic layers were washed with brine (2 × 1 L), dried over magnesium sulfate, filtered, and concentrated. The residue was first purified by column chromatography on a 3 kg silica gel column (solid deposition) with an eluent gradient of dichloromethane 100 to dichloromethane / ethyl acetate (70 / 30), and then purified a second time by column chromatography on a 1.5 kg silica gel column solid deposition with a gradient of heptane 100 to ethyl acetate 100. The collected fractions were concentrated to give an orange sticky solid. The solid was triturated in 500 ml of heptane at 50 °C for 2 hours and then filtered to give the title compound 115 g (purity 99%, yield 50%).

[0248] Separation of enantiomers Separation on a preparative scale was carried out using a SFC-PICLAB Hybrid10-150 apparatus from Pic Solution with UV detection in the range of 210 nm to 280 nm, preferably 220 to 254 nm.

[0249] (5RS)-3-[3-(3-Chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine (diastereomer mixture) (17 g, purity 99%) was separated by preparative supercritical fluid chromatography to obtain (5R)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine (8.71 g, purity 100%) and (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine (I) (8.77 g, purity 100%). Column: ChiralPak® IA, 250×20 mm; Eluent A: CO 2 ; Eluent B: methanol; Isocratic 25%. Analytical chiral HPLC. Column ChiralPak® IB N-5 150×2.15 μm; Eluent A: water + 0.1% HCOOH; Eluent B: acetonitrile + 0.1% HCOOH; Isocratic 45:55 A / B; Flow rate: 0.175 ml / min; UV: 220 nm; Oven: 25°C. (5R)-3-[3-(3-Chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine: R t = 12.33 min; Specific rotation: +79.7° (c = 1.21, CDCl 3 , 25°C), where the concentration c is expressed in g / 100 mL. (5S)-3-[3-(3-Chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine (I): R t = 13.09 min; Specific rotation: -81.4° (c = 1.16, CDCl 3 , 25°C), where the concentration c is expressed in g / 100 mL. LogP: 3.88 1 H-NMR (600.2 MHz, CDCl 3 ): δ = 7.9188 (5.3); 7.3551 (0.6); 7.3490 (0.7); 7.3445 (1.1); 7.3389 (1.2); 7.3333 (0.7); 7.3280 (0.7); 7.2619 (5.8); 7.1515 (3.6); 7.1452 (2.0); 7.1397 (2.8); 7.1100 (2.3); 7.1090 (2.3); 7.0607 (2.1); 7.0479 (2.3); 6.7461 (1.2); 6.7449 (1.2); 6.7334 (1.1); 6.7322 (1.1); 6.0010 (1.2); 4.2055 (1.0); 4.1999 (1.1); 4.1873 (1.2); 4.1817 (1.2); 4.0168 (0.4); 4.0118 (0.5); 4.0075 (0.6); 4.0045 (0.6); 4.0016 (0.6); 3.9973 (0.6); 3.9923 (0.4); 3.8732 (1.3); 3.8641 (1.2); 3.8550 (1.2); 3.8459 (1.1); 3.1400 (0.9); 3.1316 (0.9); 3.1175 (1.0); 3.1091 (1.0); 2.8832 (1.1); 2.8676 (1.1); 2.8608 (1.0); 2.8452 (0.9); 2.6415 (16.0); 2.1863 (11.5); 1.5862 (2.0); 0.0000 (7.7).

[0250] B-2. Polymorphic form B of (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine B-2-1. Preparation of polymorphic form B The compound of formula (I) was dissolved in the respective solvents (shown in Table 5) at their respective boiling points. The solution was filtered and divided into four, three, or two parts (if any, depending on the solvent used). The different parts were stored separately: a) At room temperature b) In a refrigerator (4 °C to 7 °C) c) In a freezer (-20 °C to -18 °C) Until dry d) If necessary, a poor solvent was added.

[0251]

Table 5

[0252] Examples 4 to 16 in Table 4 gave polymorphic form B. The obtained crystals of polymorphic form B were separated and analyzed by X-ray powder diffraction (XRPD), Raman, and IR spectroscopy.

[0253] B-3. Polymorphic form A of (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine B-3-1. Preparation of polymorphic form A Method for producing polymorphic form A To obtain crystals of polymorphic form A, temperature-dependent X-ray powder diffraction (XRPD) experiments were carried out to enable recrystallization at different temperatures. The changing phases were observed at 60 °C during heating and 40 °C during cooling. The X-ray diffraction pattern of polymorphic form A was observed at 75 °C.

[0254] The obtained crystals of polymorph A were separated and analyzed by X-ray powder diffraction (XRPD).

[0255] C. Characteristics of polymorphic form B of (5S)-3-[3-(3-chloro-2-fluorophenoxy)-6-methylpyridazin-4-yl]-5-(2-chloro-4-methylbenzyl)-5,6-dihydro-4H-1,2,4-oxadiazine of formula (I) C-1. Formulation Example The formulation of the compound of formula (I) in polymorphic form B was formulated as a suspension concentrate (SC) formulation according to the recipe in Table 6. The formulation was produced by first preparing a 2% gel of Rhodopol 23 in water containing a biocide. The remaining components were mixed in the following order with stirring: water, antifreeze, antifoaming agent and dispersing agent until dissolved, then the powder of polymorphic form B of the compound of formula (I) was added, dispersed by mixing and milled in a bead mill to obtain a particle size (Dv50) of 1 to 10 microns. To the milled dispersion, 2% Rhodopol 23 gel was added with low shear mixing to produce the SC formulation. Then, the formulation was subjected to a stability test by storing samples at 70 °C and 80 °C.

[0256] [Table 6]

[0257] The physical aspects were determined by visual inspection of the samples, diluting the SC formulation to about 1% and observing the microscopic images for the agglomeration state and the crystal size of polymorphic form B of the compound of formula (I) according to the present invention. The dilution stability (also called suspension property) was determined by preparing 100 ml of a 1% (volume / volume) dispersion by mixing in CIPAC C water (hardness 500 ppm) (www.cipac.org MT18.1) in a graduated cylinder having a particularly narrow end at the bottom and visualizing the volume of any precipitate after 1 hour. The measurements were carried out at room temperature.

[0258] [Table 7]

[0259] trace # means that less than 0.1 mL of particles can be observed in a sample volume of 100 mL.

[0260] The temperatures applied in Table 7 were much higher than those used in the standard procedure where the samples were run at 54 °C for 2 weeks.

[0261] The results in Table 7 show no differences in microscopic probe, appearance, and suspension after 1 week at 70 °C and 5 days at 80 °C. Specifically, with respect to suspension, the SC formulation comprising polymorphic form B of the compound of formula (I) shows only a trace amount (less than 0.1 mL) of particles even after subjecting the probe to temperatures of 70 °C (1 week) and 80 °C (5 days). These temperatures are higher than the transition temperature range of 49 °C to 66 °C. No transition to polymorph A was observed.

[0262] These results indicate that polymorph B exhibits surprisingly high stability even when subjected to temperatures higher than the transition temperature range from polymorph B to polymorph A for several days. Therefore, the SC formulation comprising polymorphic form B of the compound of formula (I) is surprisingly highly stable, preferably highly dilution-stable, more preferably highly suspension-stable, which is of great relevance as polymorphic transition is expected to cause instability of the SC formulation.

[0263] C-2. Slurry Experiment The compound of formula (I) was suspended in each solvent and stirred at 0 °C, 40 °C (Mya4 stirrer station, 250 u / min), and 80 °C (Reacti-Therm III, stirring level 6) as shown in Table 8. After 3 - 8 days, an additional amount of the solvent was added to the suspension. In two experiments, an additional substance was added after 4 days. After 8 days, the suspension was dried under environmental conditions.

[0264] The obtained crystals were isolated and analyzed by X-ray powder diffraction (XRPD) spectroscopy, DSC, and TGA. Figure 3A shows the XRPD after Slurry Experiment 3.

[0265] [Table 8]

Claims

1. Equation (I): 【Chemistry 1】 Crystallographic form B of the compound, wherein morphology B of the compound exhibits the following reflections, cited as 2θ values ​​±0.2° in an X-ray powder diffractogram at 25°C and under Cu-Kα1 radiation: 20.2, 23.3, and 25.

1.

2. Form B of the compound according to claim 1, wherein form B of the compound exhibits the following reflectances, cited as 2θ ± 0.2° in an X-ray powder diffractogram at 25°C and under Cu-Kα1 radiation: 20.2, 23.3, 25.1, 14.5, and 19.

4.

3. Form B of the compound according to claim 1, wherein form B of the compound exhibits at least the following reflectances, cited as 2θ values ​​±0.2° in an X-ray powder diffractogram at 25°C and under Cu-Kα1 radiation: 20.2, 23.3, 25.1, 14.5, 19.4, 23.4, and 10.

6.

4. Form B of the compound of formula (I) is, in the Raman spectrum, at least the following band (peak maximum value cm) －１ Form B of the compound of formula (I) according to claim 1, showing 98, 112 and 1585.

5. Form B of the compound of formula (I) is, in the Raman spectrum, at least the following band (peak maximum value cm) －１ Form B of the compound of formula (I) according to claim 1, showing ): 98, 112, 1585, 1279 and 2925.

6. Form B of the compound of formula (I) is, in the Raman spectrum, at least the following band (peak maximum value cm) －１ Form B of the compound of formula (I) according to claim 1, showing ): 98, 112, 1585, 1279, 2925, 688 and 1609.

7. A method for producing crystalline form B according to any one of claims 1 to 6, wherein the method is: a) A step of diluting the compound of formula (I) in a suitable solvent or solvent mixture, b) A step of heating the composition from step a) to a temperature of at least 70°C, c) A step of cooling the solution from step b) to a temperature of less than 20°C, A method that includes the following:

8. A composition comprising polymorph B as described in any one of claims 1 to 6.

9. The composition according to claim 8, comprising at least a) one or more drift-reducing components, b) one or more spreading agents, c) one or more uptake-promoting agents, d) one or more rain-resistant additives, e) other formulations as needed, and / or f) one or more carriers up to a predetermined volume.

10. The composition according to claim 8, wherein the composition is a suspension concentrate.

11. A plant protective agent comprising crystalline form B of formula (I) as described in any one of claims 1 to 6.

12. The plant protection agent according to claim 11, further comprising one or more additional active substances selected from the group consisting of herbicides, insecticides, acaricides, fungicides, phytotoxicity reducers (safeners), and / or plant growth regulators.

13. A composition that preferably has high stability, and more preferably high stability at a temperature higher than the transition temperature, comprising polymorph B as described in any one of claims 1 to 6.

14. A plant protective agent that preferably has high stability, more preferably high stability at a temperature higher than the transition temperature, comprising polymorph B according to any one of claims 1 to 6.

15. A composition for controlling undesirable microorganisms, comprising polymorph B as described in any one of claims 1 to 6.

16. A method for controlling undesirable microorganisms, comprising spraying polymorph B described in any one of claims 1 to 6 onto useful plants.

17. Equation (I): 【Chemistry 2】 Crystal morphology A of a compound, wherein morphology A of the compound exhibits the following reflections, cited as 2θ values ​​±0.2° in an X-ray powder diffractogram at 25°C and under Cu-Kα1 radiation: 16.9, 19.8, and 24.

5.

18. Form A of the compound according to claim 17, wherein form A of the compound exhibits the following reflectances, cited as 2θ values ​​±0.2° in an X-ray powder diffractogram at 25°C and under Cu-Kα1 radiation: 16.9, 19.8, 24.5, 14.2, and 24.

7.

19. Form A of the compound according to claim 17, wherein form A of the compound exhibits the following reflectances, cited as 2θ values ​​±0.2° in an X-ray powder diffractogram at 25°C and under Cu-Kα1 radiation: 16.9, 19.8, 24.5, 14.2, 24.7, 20.8, and 21.8.

Images