Crystal form of 1,2,4-oxadiazole fungicide and fungicide

Abstract

The present invention relates to compounds of formula (I-A) and (I-B) It relates to a crystalline form of JPEG2025523894000021.jpg66161, an (I-A)(I-B) composition containing the crystalline form, and a method for using the same as a bactericidal and fungicidal agent.

Description

Technical Field

[0001] The present invention relates to a solid form of an oxadiazole derivative, a composition containing this solid form, its use in agriculture or horticulture for controlling diseases caused by phytopathogens, particularly phytopathogenic fungi, and a method for controlling diseases in useful plants.

Background Art

[0002] WO 2017 / 055473 discloses that certain oxadiazole derivatives have microbicidal activity, particularly bactericidal and fungicidal activity.

[0003] In particular, polymorphs of the compound of formula (I-A) and polymorphs of the compound of formula (I-B) are disclosed.

Chemical Formula

[0004] Methods for preparing the compound of formula (I-A) are disclosed in WO 2018 / 177894 and WO 2020 / 212513. Methods for preparing the compound of formula (I-B) are disclosed in WO 2018 / 177894 and WO 2020 / 212513.

[0005] Pesticide compositions containing compounds (I-A) and (I-B) are generally disclosed in WO 2017 / 055473. Mixtures of this compound with bactericidal and fungicidal agents are disclosed in WO 2018 / 177894, WO 2022117653A1, WO 2022106304, and WO 2022117373.

[0006] However, the application of certain types of formulations depends on the particular form used in the preparation of the formulation, i.e., the polymorphic or amorphous form. For example, if the form used in the preparation of a suspension concentrate (SC) is not stable in such an SC formulation, polymorphic conversion may occur in the formulation, resulting in undesirable crystal growth. Such crystal growth can lead to thickening and possibly solidification of the formulation and, as a result, can be detrimental as it can cause clogging in application devices such as spray nozzles in agricultural application machinery. Therefore, the above compounds need to be in a stable crystalline form for preparing their agricultural or pharmaceutical formulations.

[0007] Novel solid forms of this compound and its isomers, compositions thereof, as well as methods for their preparation and use have been discovered herein.

[0008] In the context of the present invention, a polymorph is a particular crystalline form of a chemical compound that can exist in two or more crystalline forms in the solid state. The crystalline form of a compound contains constituent molecules arranged in a regular repeating pattern throughout three-dimensional space (in contrast, in an amorphous solid form, there is no long-range order in the positions of the molecules). Different polymorphs of a compound have different arrangements of atoms and / or molecules in their crystal structures. When the compound is a biologically active compound such as an insecticide or a fungicide / mildewicide, this difference in the crystal structure can result in different polymorphs having different chemical, physical, and biological properties. Properties that can be affected include crystal shape, density, hardness, color, chemical stability, melting point, hygroscopicity, suspensibility, dissolution rate, and bioavailability. Therefore, a particular polymorph can have properties that are more advantageous for a particular use compared to other polymorphs of the same compound. In particular, the physical, chemical, and biological properties listed above can have a significant impact on the manufacturing process and the development of formulations, the ease of combining the compound with other active ingredients and formulation components in a formulation, and the quality and efficacy of a plant treatment agent such as an insecticide or a fungicide / mildewicide. It should be noted that it is not possible to predict whether the solid state of a compound can exist as two or more polymorphs, nor is it possible to predict the properties of any of these crystalline forms.

[0009] Numerous techniques are commonly used to characterize polymorphs. For example, powder X-ray diffraction (pXRD) techniques are often used, and other techniques that can be used include differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), and Raman spectroscopy or infrared spectroscopy, nuclear magnetic resonance (NMR), gas chromatography, HPLC, and in particular single crystal X-ray diffraction. SUMMARY OF THE INVENTION MEANS FOR SOLVING THE PROBLEM

[0010] In a first aspect, the present invention provides a crystalline form of N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide (Compound I-A). [Chemical formula] (Characterized by an X-ray diffraction pattern including four or more 2θ angle values selected from the group of 11.9±0.2, 12.5±0.2, 16.5±0.2, 17.1±0.2, 19.5±0.2, 22.1±0.2, 23.9±0.2, and 24.9±0.2 at a temperature of 21 to 26°C.)

[0011] In one embodiment of the first aspect, the crystalline form of the compound of formula (I-A) is characterized by a powder X-ray diffraction pattern including six or more 2θ angle values selected from the group of 11.9±0.2, 12.5±0.2, 16.5±0.2, 17.1±0.2, 19.5±0.2, 22.1±0.2, 23.9±0.2, 24.9±0.2, 25.1±0.2, and 27.6±0.2 at a temperature of 21 to 26°C.

[0012] In another embodiment of the first aspect, the crystalline form of the compound of formula (I-A) is characterized by a powder X-ray diffraction pattern including 2θ angle values selected from the group of 6.2±0.2, 8.2±0.2, 11.9±0.2, 12.5±0.2, 16.5±0.2, 17.1±0.2, 18.9±0.2, 19.0±0.2, 19.5±0.2, 19.8±0.2, 21.4±0.2, 21.6±0.2, 22.1±0.2, 22.7±0.2, 23.5±0.2, 23.9±0.2, 24.9±0.2, 25.1±0.2, 25.5±0.2, 26.1±0.2, 26.9±0.2, 27.6±0.2, 27.6±0.2, 28.5±0.2, and 29.0±0.2 at a temperature of 21 to 26°C.

[0013] In another embodiment of the first aspect, the crystalline form of the compound of formula (I-A) has a powder X-ray diffraction pattern that is substantially the same as the powder X-ray diffraction spectrum shown at a temperature of 21 to 26°C in FIG. 1.

[0014] In another embodiment of the first aspect, the crystalline form of the compound of formula (I-A) further has a calculated density of 1.503 [g / cm -3 and is characterized by the following unit cell parameters:

[0015] [Table 1]

[0016] These unit cell parameters were collected as described in the examples. The crystalline form of the compound of formula (I-A) is further characterized by the space group of 21 / n.

[0017] In still another embodiment of the first aspect, the melting point peak of the crystalline form of the compound of formula (I-A) is a broad endotherm of water at about 38.6 °C in the DSC trace (Figure 3).

[0018] In the second aspect, the present invention provides a crystalline form of N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propenamide (Compound I-B). [Chemical formula] (Characterized by an X-ray diffraction pattern including four or more 2θ angle values selected from the group of 8.7 ± 0.2, 9.7 ± 0.2, 14.4 ± 0.2, 15.8 ± 0.2, 17.3 ± 0.2 and 20.7 ± 0.2 at a temperature of 21 to 26 °C.)

[0019] In one embodiment of the second aspect, the crystalline form of the compound of formula (I-B) is characterized by a powder X-ray diffraction pattern including six or more 2θ angle values selected from the group of 8.7 ± 0.2, 9.7 ± 0.2, 12.1 ± 0.2, 14.4 ± 0.2, 15.8 ± 0.2, 17.3 ± 0.2, 20.7 ± 0.2, 23.0 ± 0.2, 29.1 ± 0.2 and 30.0 ± 0.2 at a temperature of 21 to 26 °C.

[0020] In other embodiments of the second aspect, the crystalline form of the compound of formula (I-B) is characterized by a powder X-ray diffraction pattern comprising 2θ angle values selected from the group of 8.7±0.2, 9.7±0.2, 12.1±0.2, 13.3±0.2, 14.4±0.2, 15.2±0.2, 15.8±0.2, 16.2±0.2, 17.3±0.2, 18.5±0.2, 19.1±0.2, 20.7±0.2, 21.8±0.2, 22.1±0.2, 23.0±0.2, 23.7±0.2, 29.1±0.2 and 30.0±0.2 at a temperature of 21 to 26 °C.

[0021] In other embodiments of the second aspect, the crystalline form of the compound of formula (I-B) has a powder X-ray diffraction pattern that is substantially the same as the powder X-ray diffraction spectrum shown at a temperature of 21 to 26 °C in Figure 4.

[0022] In other embodiments of the second aspect, the crystalline form of the compound of formula (I-B) further has a calculated density of 1.434 [g / cm -3 and is characterized by the following unit cell parameters:

[0023]

Table 2

[0024] These unit cell parameters were collected as described in the examples. The crystalline form of the compound of formula (I-B) is further characterized by the space group of 21 / n.

[0025] In still other embodiments of the second aspect, the melting point peak of the crystalline form of the compound of formula (I-B) is a broad endotherm of water at about 63.5 °C in the DSC trace (Figure 6).

[0026] According to a third aspect of the present invention, there is provided a pesticidal composition comprising a crystalline form of a compound of formula (I-A) according to the first aspect of the present invention, or a crystalline form of a compound of formula (I-B) according to the second aspect, in a fungicidally and bactericidally effective amount. Such an agricultural composition may further comprise at least one additional active ingredient and / or a pesticidally acceptable diluent or carrier.

[0027] In one embodiment of the third aspect, there is provided a pesticidal composition comprising a crystalline form of a compound of formula (I-A) according to the first aspect of the present invention in a fungicidally and bactericidally effective amount. Such an agricultural composition may further comprise at least one additional active ingredient and / or a pesticidally acceptable diluent or carrier.

[0028] In another embodiment of the third aspect, there is provided a pesticidal composition comprising a crystalline form of a compound of formula (I-B) according to the second aspect of the present invention in a fungicidally and bactericidally effective amount. Such an agricultural composition may further comprise at least one additional active ingredient and / or a pesticidally acceptable diluent or carrier.

[0029] The polymorphs of the present invention can be applied in their as-is form, but more preferably, they are incorporated into pesticidal or pharmaceutical compositions, particularly pesticidal compositions, by conventional means.

[0030] According to a fourth aspect of the present invention, there is provided a method for controlling or preventing ectoparasitism of useful plants by phytopathogenic microorganisms, wherein a fungicidally and bactericidally effective amount of a crystalline form of a compound of formula (I-A) according to one aspect of the invention, or a crystalline form of a compound of formula (I-B) according to the second aspect, or a composition comprising a crystalline form of a compound of formula (I-A) or formula (I-B) according to the first aspect is applied to the plant, its parts or its habitat.

[0031] In one embodiment of the fourth aspect of the present invention, there is provided a method for controlling or preventing ectoparasitism on useful plants by phytopathogenic microorganisms, wherein a crystalline form of the compound of formula (I-A) according to the first aspect of the present invention in a bactericidal and fungicidal effective amount, or a composition containing the crystalline form of the compound of formula (I-A) according to the first aspect, is applied to a plant, a part thereof or its habitat.

[0032] In another embodiment of the fourth aspect of the present invention, there is provided a method for controlling or preventing ectoparasitism on useful plants by phytopathogenic microorganisms, wherein a crystalline form of the compound of formula (I-B) according to the second aspect of the present invention in a bactericidal and fungicidal effective amount, or a composition containing the crystalline form of the compound of formula (I-B) according to the first aspect, is applied to a plant, a part thereof or its habitat.

[0033] In other embodiments of the present invention, there is provided a method for controlling or preventing ectoparasitism of a genetically modified plant by a phytopathogenic microorganism, particularly a phytopathogenic fungus, wherein a compound of formula (I-A) or a polymorph of formula (I-A) is applied to the plant. Preferably, the genetically modified plant is a soybean plant. Examples of genetically modified soybean plants include, but are not particularly limited to, Intacta®, Intacta® 2, Intacta® Roundup Ready® 2 Pro (Intacta® RR2 PRO), Intacta® 2 Xtend®, Cultivance, Conkesta soybean, Conkesta Enlist E3® soybean, Enlist® soybean, Enlist E3® soybean, Roundup Ready® soybean, Roundup Ready® 2 Xtend®, Genuity® Roundup Ready® 2 Xtend®, Genuity® Roundup Ready 2 Yield®, herbicide-tolerant soybean lines, Optimum GAT®, Liberty Link® soybean, Vistive Gold®, Verdeca HB4 soybean, Treus®, Plenish®. More preferably, the genetically modified plant is a Bt soybean plant.Examples of "Bt plants" are, for example, soybean varieties sold under the trade names Intacta® , Intacta® 2, Intacta® Roundup Ready® 2 Pro (Intacta® RR2 PRO), Cultivance, Conkesta Soybean, Conkesta Enlist E3™ Soybean, Enlist™ Soybean, Enlist E3™ Soybean, Roundup Ready® Soybean, Genuity® Roundup Ready® 2 Xtend™, Genuity® Roundup Ready 2 Yield™, herbicide-tolerant soybean lines, Optimum GAT™, Liberty Link® Soybean, Vistive Gold™, Verdeca HB4 Soybean, Treus™, Plenish™. Even more preferably, the Bt soybean plants are selected from Intacta RR2 PRO® or Conkesta Enlist E3®.

[0034] In other embodiments of the present invention, there is provided a method for controlling or preventing ectoparasitism of a genetically modified plant by a phytopathogenic microorganism, particularly a phytopathogenic fungus, wherein a compound of formula (I-B) or a polymorph of formula (I-B) is applied to said plant. Preferably, the genetically modified plant is a soybean plant. Examples of genetically modified soybean plants include, but are not particularly limited to, Intacta®, Intacta® 2, Intacta® Roundup Ready® 2 Pro (Intacta® RR2 PRO), Intacta® 2 Xtend®, Cultivance, Conkesta soybean, Conkesta Enlist E3® soybean, Enlist® soybean, Enlist E3® soybean, Roundup Ready® soybean, Roundup Ready® 2 Xtend®, Genuity® Roundup Ready® 2 Xtend®, Genuity® Roundup Ready 2 Yield®, herbicide-tolerant soybean lines, Optimum GAT®, Liberty Link® soybean, Vistive Gold®, Verdeca HB4 soybean, Treus®, Plenish®. More preferably, the genetically modified plant is a Bt soybean plant.Examples of "Bt plants" include, for example, soybean varieties sold under the trade names Intacta® (registered trademark), Intacta® 2, Intacta® Roundup Ready® 2 Pro (Intacta® RR2 PRO), Cultivance, Conkesta soybean, Conkesta Enlist E3® soybean, Enlist® soybean, Enlist E3® soybean, Roundup Ready® soybean, Genuity® Roundup Ready® 2 Xtend®, Genuity® Roundup Ready 2 Yield®, herbicide-tolerant soybean lines, Optimum GAT®, Liberty Link® soybean, Vistive Gold®, Verdeca HB4 soybean, Treus®, Plenish®. Even more preferably, the Bt soybean plant is selected from Intacta RR2 PRO® or Conkesta Enlist E3®.

[0035] In a preferred embodiment of the present invention, a method for controlling pests in a soybean plant is provided, wherein the soybean plant is a Bt soybean plant, preferably a Bt soybean plant selected from Intacta RR2 PRO® or Conkesta Enlist E3®, and a compound of formula (I-A) is applied to the plant, its parts, its propagation material, the pest, its food source, habitat or breeding ground.

Chemical formula

[0036] In another preferred embodiment of the present invention, there is provided a method for controlling pests in soybean plants, wherein the soybean plants are Bt soybean plants, preferably Bt soybean plants selected from Intacta RR2 PRO® or Conkesta Enlist E3®, and the method comprises contacting a polymorph of the compound of formula (I-A) according to the present invention with the plant, its parts, its propagation materials, the pest, its food source, habitat or breeding ground.

[0037] In a preferred embodiment of the present invention, there is provided a method for controlling pests in soybean plants, wherein the soybean plants are Bt soybean plants, preferably Bt soybean plants selected from Intacta RR2 PRO® or Conkesta Enlist E3®, and the method comprises contacting the plant, its parts, its propagation materials, the pest, its food source, habitat or breeding ground with a compound of formula (I-B) [Chemical formula] characterized by including the step of contacting.

[0038] In another preferred embodiment of the present invention, there is provided a method for controlling pests in soybean plants, wherein the soybean plants are Bt soybean plants, and the method comprises contacting a polymorph of the compound of formula (I-B) according to the present invention with the plant, its parts, its propagation materials, the pest, its food source, habitat or breeding ground.

[0039] Examples of commercially available genetically modified soybean plants that can preferably be processed according to the present invention include Intacta®, Intacta® 2, Intacta® 2 Xtend™, Intacta® Roundup Ready® 2 Pro (Intacta® RR2 PRO), Cultivance, Conkesta Soybean, Conkesta Enlist E3™ Soybean, Enlist™ Soybean, Enlist E3™ Soybean, Roundup Ready® Soybean, Roundup Ready® 2 Xtend™, Genuity® Roundup Ready® 2 Xtend™, Genuity® Roundup Ready 2 Yield™, herbicide-tolerant soybean lines, Optimum GAT™, Liberty Link® Soybean, Vistive Gold™, Verdeca HB4 Soybean, Treus™ or Plenish™, and commercially available products such as plant seeds sold or distributed under these trade names.

[0040] Examples of commercially available Bt soybean plants that can preferably be processed according to the present invention include plant seeds sold under the trade names Intacta®、Intacta® 2、Intacta® 2 Xtend™、Intacta® Roundup Ready® 2 Pro (Intacta® RR2 PRO)、Cultivance、Conkesta Soybean、Conkesta Enlist E3™ Soybean、Enlist™ Soybean、Enlist E3™ Soybean、Roundup Ready® Soybean、Roundup Ready® 2 Xtend™、Genuity® Roundup Ready® 2 Xtend™、Genuity® Roundup Ready 2 Yield™、herbicide-tolerant soybean lines、Optimum GAT™、Liberty Link® Soybean、Vistive Gold™、Verdeca HB4 Soybean、Treus™ or Plenish™, etc.

[0041] Preferably, the genetically modified soybean plants that can be processed according to the present invention are selected from Intacta RR2 PRO® or Conkesta Enlist E3®.

[0042] According to a fifth aspect of the present invention, there is provided the use of a crystalline form of the compound of formula (I-A) according to the first aspect of the present invention, or a crystalline form of the compound of formula (I-B) according to the second aspect, as a fungicidal and antimycotic agent. According to this aspect of the present invention, this use may exclude methods of treating the body of a human or animal by surgery or therapy.

[0043] In one embodiment of the fifth aspect of the present invention, there is provided the use of a crystalline form of the compound of formula (I-A) according to the first aspect of the present invention as a fungicidal and antimycotic agent. According to this aspect of the present invention, this use may exclude methods of treating the body of a human or animal by surgery or therapy.

[0044] In another embodiment of the fifth aspect of the present invention, there is provided the use of a crystalline form of the compound of formula (I-B) according to the second aspect of the present invention as a bactericidal and fungicidal agent. According to this aspect of the present invention, this use may exclude methods of treating the human or animal body by surgery or therapy.

[0045] In other embodiments of the present invention, there is provided the use of a compound of formula (I-A) or a polymorph thereof (I-A) for controlling phytopathogenic fungi in a genetically modified plant. Preferably, the genetically modified plant is a soybean plant. More preferably, the genetically modified soybean plant is a Bt soybean plant, and even more preferably, a Bt soybean plant selected from Intacta RR2 PRO® or Conkesta Enlist E3®.

[0046] In other embodiments of the present invention, there is provided the use of a compound of formula (I-B) or a polymorph thereof (I-B) for controlling phytopathogenic fungi in a genetically modified plant. Preferably, the genetically modified plant is a soybean plant. More preferably, the genetically modified soybean plant is a Bt soybean plant, and even more preferably, a Bt soybean plant selected from Intacta RR2 PRO® or Conkesta Enlist E3®.

[0047] In other embodiments of the present invention, there is provided the use of a compound of formula (I-A) or a polymorph thereof (I-A) for controlling Phakopsora pachyrhizi in a genetically modified plant. Preferably, the genetically modified plant is a soybean plant. More preferably, the genetically modified soybean plant is a Bt soybean plant, and even more preferably, a Bt soybean plant selected from Intacta RR2 PRO® or Conkesta Enlist E3®.

[0048] In another embodiment of the present invention, there is provided the use of a compound of formula (I-B) or a polymorph thereof (I-B) for controlling Phakopsora pachyrhizi in a genetically modified plant. Preferably, the genetically modified plant is a soybean plant. More preferably, the genetically modified soybean plant is a Bt soybean plant, and even more preferably, a Bt soybean plant selected from Intacta RR2 PRO® or Conkesta Enlist E3®.

[0049] In a preferred embodiment of the present invention, there is provided the use of a compound of formula (I-A) for controlling a phytopathogenic fungus in a genetically modified soybean plant

Chemical formula

[0050] In a preferred embodiment of the present invention, there is provided the use of a compound of formula (I-A) for controlling Phakopsora pachyrhizi in a genetically modified soybean plant

Chemical formula

[0051] In another preferred embodiment of the present invention, there is provided the use of a polymorph of the compound of formula (I-A) according to the present invention for controlling Phakopsora pachyrhizi in a genetically modified soybean plant. Preferably, the genetically modified soybean plant is a Bt soybean plant, preferably a Bt soybean plant selected from Intacta RR2 PRO® or Conkesta Enlist E3®.

[0052] In a preferred embodiment of the present invention, there is provided the use of a compound of formula (I-B) for controlling a phytopathogenic fungus in a genetically modified soybean plant

Chemical formula

[0053] In a preferred embodiment of the present invention, there is provided the use of a compound of formula (I-B) for controlling Phakopsora pachyrhizi in a genetically modified soybean plant

Chemical formula

[0054] In another preferred embodiment of the present invention, there is provided the use of a polymorph of a compound of formula (I-B) according to the present invention for controlling Phakopsora pachyrhizi in a genetically modified soybean plant. Preferably, the genetically modified soybean plant is a Bt soybean plant, preferably a Bt soybean plant selected from Intacta RR2 PRO® or Conkesta Enlist E3®.

[0055] Examples of commercially available genetically modified soybean plants that can preferably be treated according to the present invention include those sold or distributed under the trade names Roundup Ready® (RR1), Roundup Ready 2 Xtend®, Roundup Ready 2 Yield®, XtendFlex®, Intacta RR2 PRO®, Intacta 2 Xtend®, Vistive® Gold™, Conkesta Enlist E3®, Conkesta E3®, Enlist E3®, Genuity® Roundup Ready 2 Yield™, Genuity® Roundup Ready® 2 Xtend™, herbicide-tolerant soybean lines, Optimum GAT™, Liberty Link™ soybeans, Vistive Gold™, Verdeca HB4 soybeans, Treus™, or Plenish™, such as plant seeds.

[0056] Preferably, the genetically modified soybean plant that can be treated according to the present invention is selected from Intacta RR2 PRO® or Conkesta Enlist E3®.

[0057] As used herein, the term "control" refers to a reduction in the number of pests, the extermination of pests, and / or the prevention of further damage by pests such that damage to the plant or plant-derived products is reduced.

[0058] As used herein, the term "pest" refers to insects and mollusks found in agriculture, horticulture, forestry, the storage of plant-derived products (such as fruits, grains, and lumber); and pests associated with damage to man-made structures. The term "pest" includes all stages in the life cycle of the pest.

[0059] As used herein, the term "crop" should be understood to include crop plants transformed using recombinant DNA technology such that they are capable of synthesizing one or more selectively acting toxins, such as those known from toxin production, particularly those from the genus Bacillus.

[0060] As used herein, the terms "genetically modified plant" or "genetically modified soybean plant" refer to a plant or soybean plant in which the genetic material has been modified in a way that does not occur naturally by gradient and / or natural recombination. These plants are also referred to as transgenic or genetically modified plants. Genetic modification of plants includes adding a specific DNA sequence to the plant's genome to confer new or different characteristics. This can include changing the way the plant grows or conferring resistance to specific diseases. Examples of genetically modified soybean plants are available under the trade names YIELD GARD®, Intacta®, Intacta® 2, Intacta® Roundup Ready® 2 Pro (Intacta® RR2 PRO), Cultivance, Conkesta Soybean, Conkesta Enlist E3™ Soybean, Enlist™ Soybean, Enlist E3™ Soybean, Roundup Ready® Soybean, Genuity® Roundup Ready® 2 Xtend™, Genuity® Roundup Ready 2 Yield™, herbicide-tolerant soybean lines, Optimum GAT™, Liberty Link® Soybean, Vistive Gold™, Verdeca HB4 Soybean, Treus™, Plenish™.

[0061] As used herein, the term "Bt soybean plant" refers to a genetically modified soybean plant that produces an insecticidal protein naturally produced by a bacterial species of Bacillus thuringiensis, such as the CrylA(a), CrylA(b), CrylA(c), CryllA, CrylllA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb, and CrylF genes, and combinations thereof. These soybeans, which have been genetically modified to produce the same toxin as Bacillus thuringiensis (Bt) in all cells of the plant for the purpose of protecting soybeans from pests, are referred to herein as "Bt soybeans". Examples of Bt soybean plants are Intacta RR2 PRO® or Conkesta Enlist E3®.

[0062] As used herein, the term "effective amount" refers to the amount of a compound or a salt thereof that produces a desired effect upon single or multiple applications.

[0063] As used herein, the term "room temperature" or "RT" or "rt" or "ambient temperature" refers to a temperature of about 15°C to about 35°C. For example, rt can refer to a temperature of about 20°C to about 30°C.

[0064] The effective amount can be readily determined by one of ordinary skill in the art using known techniques and observing what is obtained under similar circumstances. In determining the effective amount, numerous factors are considered, including but not limited to the type of plant or plant-derived product to which it is applied; the pest to be controlled and its life cycle; the particular compound being applied; the method of application; and other relevant circumstances.

[0065] The compounds of formula (I-A) and (I-B) according to the present invention can be formed as shown in the following scheme (Scheme 1).

[0066] The compounds of formula (I-A) and (I-B) are prepared according to the process of the present invention, which process comprises reacting a compound of formula (II-A) or (II-B) with a compound of formula (III) or a compound of formula (IV). This reaction is shown in Scheme 1.

Chemical formula

[0067] For the purposes of the present invention, the compounds of formula (II) are used in any of their tautomeric forms having different (E) / (Z) configurations in the process of the present invention.

[0068] Examples of compounds of formula (III) suitable for use in the process of the present invention are those in which R 1 is selected from methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl and isobutyl. Preferably, R 1 in the compound of formula (III) is methyl or ethyl. The compound of formula (III) is more preferably methyl 2,2,2-trifluoroacetate or ethyl 2,2,2-trifluoroacetate.

[0069] Alternatively, examples of compounds of formula (III) suitable for use in the process of the present invention are those in which R 1 is selected from hydrogen or alkyl-C(=O)-alkyl. Examples of compounds of formula (III) suitable for use in the process of the present invention include trifluoroacetic acid, trifluoroacetic acid esters, trifluoroacetic anhydride.

[0070] Examples of compounds of formula (IV) suitable for use in the process of the present invention include those in which the halogen is selected from chloride, bromide or fluoride. The compound of formula (IV) is preferably trifluoroacetyl chloride.

[0071] Alternatively, a compound of formula (I-A) or (I-B) can be prepared from a compound of formula (II-A) or (II-B) via reaction with trifluoroacetic acid, a trifluoroacetic acid ester, trifluoroacetic anhydride or a trifluoroacetyl halide (including trifluoroacetyl fluoride, trifluoroacetyl chloride, and trifluoroacetyl bromide) in the presence of an optional base (e.g., pyridine or 4-dimethylaminopyridine) in a suitable solvent (e.g., toluene, ethyl acetate, tetrahydrofuran, 2-methyltetrahydrofuran or ethanol) at a temperature of 0 °C to 75 °C. For related examples, see WO 2003 / 028729, WO 2017 / 055473, and WO 2010 / 045251.

[0072] In an embodiment of the process of the present invention, a compound of formula (I-A) or (I-B) is preferably prepared from a compound of formula (II), (II-A) or (II-B) via reaction with 1.0 to 2.0 equivalents of a compound of formula (III).

[0073] In a preferred embodiment of the present invention, the process of the present invention is carried out in the presence of at least one base.

[0074] According to one embodiment, the process of the present invention is carried out in the presence of at least one base and optionally at least one solvent.

[0075] Examples of suitable bases include inorganic bases and organic bases. Preferred bases are tertiary amines, substituted or unsubstituted pyridines, bicyclic amines and mixtures thereof, NaH, alkali hydroxides, alkali metal C1-6 alkoxylates and alkaline earth metal C1-6 alkoxylates, such as sodium methoxide, sodium hydroxide, sodium ethoxide, sodium tert-butoxide, potassium tert-butoxide, potassium pentoxide, potassium carbonate (K2CO3), sodium carbonate (Na2CO3), sodium bicarbonate (NaHCO3), triethylamine and 3,5-lutidine or 2,6-lutidine, and the like, selected from the group consisting of.

[0076] As used herein, the term "alkali metal" refers to the elements of Group 1 of the periodic table, preferably lithium (Li), sodium (Na) or potassium (K).

[0077] As used herein, the term "alkaline earth metal" refers to the elements of Group 2 of the periodic table, preferably magnesium (Mg) or calcium (Ca).

[0078] Examples of suitable solvents include, for example, aromatic solvents such as toluene, xylene and dichlorobenzene, or polar solvents such as tetrahydrofuran (THF) and dimethyl carbonate (DMC), or non-polar solvents such as methylcyclohexane (MCH).

[0079] Further examples of solvents include, but are not particularly limited to, methanol, ethanol, tert-butanol, 2-methyltetrahydrofuran, N,N-dimethylformamide, dimethyl sulfoxide, pyridine, pyrrolidine, N-methyl-2-pyrrolidone, toluene and dioxane.

[0080] The process of the present invention is usually carried out at a temperature of 0 °C to 60 °C, preferably 0 °C to 40 °C, more preferably 0 °C to 25 °C, or more preferably 25 to 40 °C. Very good results were obtained when the process of the present invention was carried out at a temperature of 0 °C to 25 °C, or 25 to 40 °C.

[0081] The process of the present invention is usually carried out at a pressure of 1 atm to 5 atm (the atmospheric pressure abbreviated as atm is a unit of pressure equal to the average atmospheric pressure at sea level).

[0082] Typical reaction times are usually in the range of 1 to 16 hours. Very good results were obtained when the process of the present invention was carried out with a reaction time of 1 to 2 hours.

[0083] Typically, the process disclosed in Scheme 1 further includes the step of isolating the compound of formula (I-A) or (I-B) using an aqueous medium. Advantageously, the compound of formula (I-A) or (I-B) is isolated from the reaction mixture using an aqueous medium, typically by post-extraction treatment.

[0084] In a preferred embodiment of the process of the present invention, the aqueous medium is an aqueous acidic medium. The aqueous acidic medium is generally prepared by adding one or more acids to the aqueous medium. Preferably, the process of the present invention further includes the step of isolating the compound of formula (I-A) or (I-B) using the aqueous acidic medium.

[0085] During the post-reaction treatment, it has been found that the aqueous acidic medium can provide the most suitable medium for the purification of the compound of formula (I-A) or (I-B). In particular, it has been unexpectedly found that by adding the aqueous acidic medium to the reaction mixture, it is possible to achieve an improvement in the isolation yield.

[0086] Typically, the aqueous acidic medium contains an acid selected from the group consisting of acetic acid, citric acid, sulfuric acid, hydrochloric acid (HCl), HCl / water, and HCl / dioxane. Preferably, the aqueous acidic medium contains citric acid.

[0087] The aqueous acidic medium preferably has a pH of 2.0 to 6.0, more preferably 4.9.

[0088] The method for preparing the compound of formula (II-A) is disclosed in International Publication No. WO 2018 / 177894 and International Publication No. WO 2020 / 212513. The method for preparing the compound of formula (II-B) is disclosed in International Publication No. WO 2018 / 177894 and International Publication No. WO 2020 / 212513.

[0089] The method for preparing the compound of formula (I-A) is disclosed in International Publication No. WO 2018 / 177894 and International Publication No. WO 2020 / 212513. The method for preparing the compound of formula (I-B) is disclosed in International Publication No. WO 2018 / 177894 and International Publication No. WO 2020 / 212513.

[0090] The oil obtained for the compound of formula (I-A) was dissolved in a suitable solvent, for example, a non-polar solvent such as methylcyclohexane, and the solution was cooled until crystal growth occurred. The obtained crystals were filtered and washed with a suitable solvent, for example, a non-polar solvent such as methylcyclohexane, although not particularly limited thereto, to obtain a white crystalline product.

[0091] It has been found that the use of a non-polar solvent for the crystallization of the compound of formula (I-A) or (I-B) was advantageous.

[0092] Suitable solvents are, in particular, aromatic and aliphatic hydrocarbons which may or may not be substituted (by substantially non-polar groups), and the choice thereof is mainly determined from an economic point of view. Examples of suitable non-polar solvents are benzene, toluene, n-pentane, n-hexane, n-octane, methylcyclohexane or cyclohexane.

[0093] In particular, surprisingly, it has been found that the crystalline form of the compound of formula (I-A) can be obtained by the above-described method. In the crystalline form of compound (I-A), advantages such as improved work-up (filterability, purity) are brought about as compared with the oil obtained by the methods disclosed in International Publication No. 2018 / 177894 and International Publication No. 2020 / 212513, and as a result, the biological activity is improved.

[0094] The oil or solid form obtained for the compound of formula (I-B) was dissolved in a suitable solvent, for example, a non-polar solvent such as methylcyclohexane, although not particularly limited thereto, and the solution was cooled until crystal growth occurred. The obtained crystals were filtered and washed with a suitable solvent, for example, a non-polar solvent such as methylcyclohexane, to obtain a white crystalline product.

[0095] The existence of the polymorphs of the compounds of formula (I-A) and formula (I-B) of the present invention was confirmed by single crystal X-ray diffraction analysis.

[0096] A pesticidal composition comprising a polymorphic form or a compound of formula (I-A) or a compound of formula (I-B) has a very advantageous activity spectrum for protecting animals and useful plants against fungal damage and injury, in particular for protecting useful plants against fungal damage and injury.

[0097] In particular, the use of specific polymorphs of the compound (I-A) or compound (I-B) of the present invention may enable the use of new formulations as compared to the existing polymorphic / amorphous / oily forms of the compound. This can be advantageous for many reasons. For example, a suspension concentrate (SC) formulation may be more preferred than an emulsion concentrate (EC), as the SC does not contain solvents, which often means that the formulation is highly likely to be less phytotoxic than an equivalent EC formulation. However, if the existing form of the compound is not stable in such an SC formulation, polymorphic transformation can occur, leading to undesirable crystal growth. Such crystal growth is harmful as it can cause, for example, thickening and possibly solidification of the formulation, causing clogging in application devices such as spray nozzles in agricultural application machinery. These problems are overcome by using stable polymorphic forms.

[0098] An even more particularly advantageous use of specific polymorphs of the compound (I-A) or compound (I-B) of the present invention can lead to an improvement in the purity of the final product by reducing the amount and number of impurities in the specific polymorphs of the compound (I-A) or compound (I-B) of the present invention.

[0099] Analysis of the solid phase for the presence of crystals can be carried out by conventional methods known in the art. For example, it is simple and common to use powder X-ray diffraction techniques. Other techniques that can be used include differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), and Raman spectroscopy or infrared spectroscopy, NMR, gas chromatography or HPLC. Single crystal X-ray diffraction is particularly useful for identifying crystal structures.

[0100] The polymorphs of the present invention can be applied in their original form, but more preferably, they are formulated into pesticidal compositions by conventional means. Accordingly, in a further aspect, the present invention provides a pesticidal composition comprising the polymorphs of the present invention as defined above, and at least one agriculturally acceptable carrier or diluent.

[0101] In addition, the composition of the present invention may contain the polymorphs of the present invention according to the first or second aspect. In one embodiment, the composition of the present invention may contain the polymorphs of the present invention according to the first aspect. In other embodiments, the composition of the present invention may contain the polymorphs of the present invention according to the second aspect.

[0102] The pesticidal composition containing the polymorphs of the present invention is an active ingredient that is useful prophylactically and / or therapeutically in the field of pest control even at low application rates, has a favorable biocidal range, and shows good tolerance in warm-blooded species, fish, and plants. The composition of the present invention can act on not only ordinary sensitive animal pests such as representatives of insects or Acarina, but also all or individual developmental stages of resistant animal pests. The insecticidal or acaricidal activity of the composition may appear directly, for example, as the death of pests occurring immediately or after some time, for example during molting, or indirectly, for example, as a decrease in the oviposition rate and / or hatching rate, and good activity corresponds to a mortality rate (lethality) of at least 50-60%.

[0103] Thus, the pesticidal composition containing the polymorphs or a plurality of polymorphs of the present invention can be used for controlling phytopathogenic insects in a number of plant species. Accordingly, the present invention also provides a method for preventing or controlling insect infection in a plant or plant propagation material, the method comprising treating the plant or plant propagation material with an insecticidally effective amount of the agricultural composition of the present invention.

[0104] A diastereomeric or racemic mixture of a compound of formula (I-A) or (I-B) can be separated into pure diastereomers or racemic compounds by known methods based on the physicochemical differences of the components, in the free or salt form, depending on which starting materials and procedures are selected, for example by fractional crystallization, distillation and / or chromatography.

[0105] Enantiomeric mixtures such as racemic compounds, which can be obtained in a similar manner, can be separated into the desired enantiomers, for example, by recrystallization from an optically active solvent; by chromatography on a chiral adsorbent, for example, high performance liquid chromatography (HPLC) on acetylcellulose using a suitable microorganism; by cleavage with a specific immobilized enzyme through the formation of an inclusion compound, for example, using a chiral crown ether, in which only one enantiomer is complexed; or by reacting a basic end product racemic compound with an optically active acid such as a carboxylic acid such as camphoric acid, tartaric acid or malic acid, or a sulfonic acid such as camphorsulfonic acid, and separating the resulting diastereomeric mixture, for example, by fractional crystallization according to its different solubilities, to obtain a diastereomer from which the desired enantiomer can then be liberated, for example, by the action of a suitable agent such as a basic drug, and can be resolved into enantiomers by known methods such as conversion to diastereomeric salts.

[0106] Pure diastereomers or enantiomers can be obtained not only by separating suitable isomeric mixtures according to the invention, but also by diastereoselective or enantioselective syntheses, which are generally known methods, for example, by carrying out the process according to the invention using starting materials having suitable stereochemistry.

[0107] When individual components have different biological activities, it is advantageous to isolate or synthesize in each case the more biologically effective isomers, such as enantiomers or diastereomers, or mixtures of isomers, such as enantiomer mixtures or diastereomer mixtures.

[0108] As an example, a compound having two or more asymmetric carbon atoms can exist in diastereomeric forms that can be optionally separated, for example, using supercritical fluid chromatography (SFC) chromatography with a chiral column. Such diastereomers can exhibit different fungicidal and antifungal activity profiles, but all isomers and diastereomers form part of the present invention.

[0109] Polymorphs of the compounds of formula (I-A) or (I-B), and, where appropriate, their tautomers, are available in each case in free or salt form, and, where appropriate, also in the form of hydrates, and / or can contain other solvents, such as those that could have been used for the crystallization of the compounds present, for example, in solid form.

[0110] The polymorphs of the compounds of formula (I-A) and (I-B) of the present invention have a very advantageous level of biological activity for practically protecting plants from diseases caused by fungi.

[0111] The polymorphs of the compounds of formula (I-A) and (I-B) according to the present invention can be used as active ingredients in the agricultural sector and related fields of use, for example, for controlling phytopathogenic organisms or non-living materials, or for controlling putrefactive microorganisms or organisms that are potentially harmful to humans. The novel compounds are outstanding due to their excellent activity at low application rates, excellent tolerance by plants, and safety to the environment. They have very useful therapeutic, prophylactic, and transdermal properties and can be used for the protection of numerous cultivated plants. The polymorphs of the compounds of formula (I-A) and (I-B) can be used to inhibit or control pests occurring on different crops of useful plants or parts of plants (fruits, flowers, leaves, stems, tubers, roots), and on the other hand, to simultaneously protect these parts of the subsequently growing plants, for example, from phytopathogenic microorganisms.

[0112] The present invention further relates to a method for controlling or preventing infestation of plants or plant propagation materials susceptible to damage by microorganisms and / or harvested edible crops by treating the plants or plant propagation materials and / or harvested edible crops, wherein an effective amount of a polymorph of a compound of formula (I-A) or (I-B) according to the present invention is applied to the plant, a part thereof, or its habitat.

[0113] In one embodiment, the present invention relates to a method for controlling or preventing infestation of plants or plant propagation materials susceptible to microbial damage and / or harvested edible crops by treating the plants or plant propagation materials and / or harvested edible crops, wherein an effective amount of a polymorph of a compound of formula (I-A) according to the first aspect of the present invention is applied to the plant, a part thereof, or its habitat.

[0114] In another embodiment, the present invention relates to a method for controlling or preventing infestation of plants or plant propagation materials susceptible to microbial damage and / or harvested edible crops by treating the plants or plant propagation materials and / or harvested edible crops, wherein an effective amount of a polymorph of a compound of formula (I-B) according to the second aspect of the present invention is applied to the plant, a part thereof, or its habitat.

[0115] Polymorphs of the compounds of formula (I-A) or (I-B) according to the present invention can also be used as fungicides and bactericides. The term "fungicide and bactericide" as used herein means a compound that controls, modifies or prevents the growth of fungi. When used, the term "fungicidally and bactericidally effective amount" means the amount of such a compound or combination of such compounds that can effect the growth of fungi. The control or modification effect includes all deviations from natural development such as death, retardation, etc., and prevention includes barriers or other defense formations in plants to prevent infection by fungi.

[0116] Polymorphs of the compounds of formula (I-A) or (I-B) according to the present invention can be used as active ingredients in the agricultural sector and related fields of use, for example, for the control of plant pests or abiotic materials, and for the control of spoilage microorganisms or organisms that are potentially harmful to humans. The novel compounds are outstanding due to their excellent activity at low application rates, excellent tolerance by plants, and being safe for the environment. They have very useful therapeutic, prophylactic and permeation transfer properties and can be used for the protection of numerous cultivated plants. Polymorphs of the compounds of formula (I-A) or (I-B) can be used to inhibit or control pests occurring on different crops of useful plants or parts of plants (fruits, flowers, leaves, stems, tubers, roots), and on the other hand, at the same time, to protect these parts of the plants that grow later, for example, from phytopathogenic microorganisms.

[0117] Furthermore, polymorphs of the compounds of formula (I-A) or (I-B) according to the present invention can be used, for example, for the control of fungi in related fields such as the protection of industrial materials including wood and wood-based industrial products, food storage, and hygiene management.

[0118] In addition, the present invention can be used, for example, to protect abiotic materials such as lumber, wallboards and paints from damage by fungi.

[0119] The polymorphs of the compounds of formula (I-A) or (I-B) according to the present invention are effective against, for example, fungi and fungal vectors associated with diseases and phytopathogenic bacteria and viruses.

[0120] The polymorphs of the present invention can be used to control plant diseases caused by a wide range of fungal plant pathogens in the classification of Basidiomycetes, Ascomycetes, Oomycetes and / or Deuteromycetes, Blasocladiomycete, Chrytidiomycete, Glomeromycete and / or Mucoromycete.

[0121] The composition is effective in controlling a wide range of plant diseases such as leaf pathogens of ornamental crops, lawns, vegetables, field crops, cereals and fruit crops.

[0122] These pathogens may include the following: oomycete diseases including Phytophthora caused by Phytophthora capsici, Phytophthora infestans, Phytophthora sojae, Phytophthora fragariae, Phytophthora nicotianae, Phytophthora cinnamomi, Phytophthora citricola, Phytophthora citrophthora, Phytophthora erythroseptica, etc.; Pythium diseases caused by Pythium aphanidermatum, Pythium arrhenomanes, Pythium graminicola, Pythium irregulare, Pythium ultimum, etc.; diseases caused by Peronosporales such as Peronospora destructor, Peronospora parasitica, Plasmopara viticola, Plasmopara halstedii, Pseudoperonospora cubensis, Albugo Candida, Sclerophthora macrospora, Bremia lactucae, etc.and others such as Aphanomyces cochlioides, Labyrinthula zosterae, Peronosclerospora sorghi, and Sclerospora graminicola; Ascomycetes including the following, for example, Stemphylium solani, Stagonospora tainanensis, Spilocaea oleaginea, Setosphaeria turcica, Pyrenochaeta lycoperisici, Pleospora herbarum, Phoma destructiva, Phaeosphaeria herpotrichoides, Phaeocryptocus gaeumannii, Ophiosphaerella graminicola, Ophiobolus graminis, Leptosphaeria maculans, Hendersonia creberrima, Helminthosporium triticirepentis, Setosphaeria turcica, Drechslera glycines, Didymella bryoniae, Cycloconium oleagineum, Corynespora cassiicola, Cochliobolus sativus, Bipolaris cactivora, Venturia inaequalis, Pyrenophora teres, Pyrenophora tritici-repentis, Alternaria alternata, Alternaria brassicicola, AlternariaPleosporales such as Alternaria solani and Alternaria tomatophila, Septoria tritici, Septoria nodorum, Septoria glycines, Cercospora arachidicola, Cercospora sojina, Cercospora zeae-maydis, Cercosporella capsellae and Cercosporella herpotrichoides, Capnodiales such as Cladosporium carpophilum, Cladosporium effusum, Passalora fulva, Cladosporium oxysporum, Dothistroma septosporum, Isariopsis clavispora, Mycosphaerella fijiensis, Mycosphaerella graminicola, Mycovellosiella koepkeii, Phaeoisariopsis bataticola, Pseudocercospora vitis, Pseudocercosporella herpotrichoides, Ramularia beticola, Ramularia collo-cygni, Gaeumannomyces graminis, MagnaportheMagnaporthe grisea, Pyricularia oryzae, and other Magnaporthales such as Anisogramma anomala, Apiognomonia errabunda, Cytospora platani, Diaporthe phaseolorum, Discula destructiva, Gnomonia fructicola, Greeneria uvicola, Melanconium juglandinum, Phomopsis viticola, Sirococcus clavigignenti-juglandacearum, Tubakia dryina, Dicarpella spp., Valsa ceratosperma, and other Diaporthales, as well as Actinothyrium graminis, Ascochyta pisi, Aspergillus flavus, Aspergillus fumigatus, Aspergillus nidulans, Asperisporium caricae, Blumeriella jaapii, Candida spp., Capnodium ramosum, Cephaloascus spp., Cephalosporium gramineum, Ceratocystis paradoxa, Chaetomiumspp.), Hymenoscyphus pseudoalbidus, Coccidioides spp., Cylindrosporium padi, Diplocarpon malae, Drepanopeziza campestris, Elsinoe ampelina, Epicoccum nigrum, Epidermophyton spp., Eutypa lata, Geotrichum candidum, Gibellina cerealis, Gloeocercospora sorghi, Gloeodes pomigena, Gloeosporium perennans; Gloeotinia temulenta, Griphospaeria corticola, Kabatiella lini, Leptographium microsporum, Leptosphaerulinia crassiasca, Lophodermium seditiosum, Marssonina graminicola, Microdochium nivale, Monilinia fructicola, Monographella albescens, Monosporascus cannonballus, Naemacyclus spp., Ophiostoma novo-ulmi, Paracoccidioides brasiliensis, Penicillium expansum, Pestalotia rhododendri, Petriellidium spp., Pezicula spp., Phialophora gregata, Phyllachora pomigena, Phymatotrichum omnivora, Physalospora abditaabdita), Plectosporium tabacinum, Polyscytalum pustulans, Pseudopeziza medicaginis, Pyrenopeziza brassicae, Ramulispora sorghi, Rhabdocline pseudotsugae, Rhynchosporium secalis, Sacrocladium oryzae, Scedosporium spp., Schizothyrium pomi, Sclerotinia sclerotiorum, Sclerotinia minor; Sclerotium spp., Typhula ishikariensis, Seimatosporium mariae, Lepteutypa cupressi, Septocyta ruborum, Sphaceloma perseae, Sporonema phacidioides, Stigmina palmivora, Tapesia yallundae, Taphrina bullata, Thielviopsis basicola, Trichoseptoria fructigena, Zygophiala jamaicensis, and other such things caused by, such as, Blumeria graminis, Erysiphepowdery mildew caused by Erysiphales such as Golovinomyces cichoracearum, Leveillula taurica, Microsphaera diffusa, Oidiopsis gossypii, Phyllactinia guttata, Oidium arachidis, Uncinula necator, Sphaerotheca fuligena, Podosphaera leucotricha, Podospaera macularis; molds caused by Botryosphaeriales such as Dothiorella aromatica, Diplodia seriata, Guignardia bidwellii, Botrytis cinerea, Botryotinia allii, Botryotinia fabae, Fusicoccum amygdali, Lasiodiplodia theobromae, Macrophoma theicola, Macrophomina phaseolina, Phyllosticta cucurbitacearum; for example, anthracnose caused by Colletotrichum such as Colletotrichum gloeosporioides, Colletotrichum lagenarium, Colletotrichum gossypii, GlomerellaAnthracnose caused by, for example, Glommerelales such as Glomerella cingulata and Colletotrichum graminicola; and wilt or blight caused by, for example, Hypocreales such as Acremonium strictum, Claviceps purpurea, Fusarium culmorum, Fusarium graminearum, Fusarium virguliforme, Fusarium oxysporum, Fusarium subglutinans, Fusarium oxysporum f.sp. cubense, Gerlachia nivale, Gibberella fujikuroi, Gibberella zeae, Gliocladium spp., Myrothecium verrucaria, Nectria ramulariae, Trichoderma viride, Trichothecium roseum, and Verticillium theobromae; Basidiomycetes including the following, such as smut diseases caused by the Ustilaginales, for example, Ustilaginoidea virens, Ustilago nuda, Ustilago tritici, Ustilago zeae, etc., such as Cerotelium fici, Chrysomyxa arctostaphyli, Coleosporium ipomoeae, Hemileia vastatrix, Puccinia arachidis, Puccinia cacabata, Puccinia graminis, Puccinia recondita, Puccinia sorghi, Puccinia hordei, Puccinia striiformis f.sp. hordei, Puccinia striiformis f.sp. secalisrust diseases such as those caused by Pucciniales such as Puccinia secalis, Pucciniastrum coryli, or Uredinales such as Cronartium ribicola, Gymnosporangium juniperi-viginianae, Melampsora medusae, Phakopsora pachyrhizi, Phragmidium mucronatum, Physopella ampelosidis, Tranzschelia discolor, and Uromyces viciae-fabae; and other rots and diseases such as those caused by Cryptococcus spp., Exobasidium vexans, Marasmiellus inoderma, Mycena spp., Sphacelotheca reiliana, Typhula ishikariensis, Urocystis agropyri, Itersonilia perplexans, Corticium invisum, Laetisaria fuciformis, Waitea circinata, Rhizoctonia solani, Thanetephorus cucurmeris, Entyloma dahliae, Entylomella microspora, Neovossia moliniae, and Tilletia caries. Blastocladiomycetes such as Physoderma maydis; Mucoromycetes such as Choanephora cucurbitarum; species of the genus Mucor; Rhizopus arrhizus; And diseases caused by other species and genera closely related to those listed above.

[0123] In addition to these bactericidal and fungicidal activities, the composition may also be active against bacteria such as Erwinia amylovora, Erwinia caratovora, Xanthomonas campestris, Pseudomonas syringae, Strptomyces scabies, and other related species, as well as certain protozoa.

[0124] The composition according to the invention is particularly effective against phytopathogenic fungi belonging to the following classifications: Ascomycetes (e.g., Venturia, Podosphaera, Erysiphe, Monilinia, Mycosphaerella, Uncinula); Basidiomycetes (e.g., Hemileia, Rhizoctonia, Phakopsora, Puccinia, Ustilago, Tilletia); Imperfect fungi (also known as Deuteromycetes; e.g., Botrytis, Helminthosporium, Rhynchosporium, Fusarium, Septoria, Cercospora, Alternaria, Pyricularia, and Pseudocercosporella); Oomycetes (e.g., Phytophthora, Peronospora, Pseudoperonospora, Albugo, Bremia, Pythium, Pseudosclerospora, Plasmopara).

[0125] In a preferred embodiment, the polymorphs of the compounds of the invention of the following formulas (I-A) and (I-B) and mixtures thereof can be used for the following crops and pests as listed above.

[0126] Preferably, the polymorphs of the compounds of formula (I-A) and (I-B) and mixtures thereof according to the invention are suitable for the control of the following fungal diseases in soybeans and genetically modified soybeans, such as Bt soybeans, as listed above: species of Alternaria (Alternaria spp.) (Alternaria leaf spot); species of Cercospora (Cercospora spp.) (Cercospora leaf spot), such as C. sojina or C. kikuchii, species of Colletotrichum (Colletotrichum spp.) (sexual generation: species of Glomerella (Glomerella spp.)) (anthracnose), such as C. truncatum or C. gloeosporioides, Corynespora cassiicola (leaf spot); Dematophora (sexual generation: Rosellinia) necatrix (root rot and sclerotinia); species of Diaporthe, such as D. phaseolorum (damping-off); species of Fusarium (Fusarium spp.) (sexual generation: species of Gibberella (Gibberella spp.)) (wilt, root rot or sclerotinia), such as, respectively, F. tucumaniae and F. brasiliense, which cause sudden death syndrome in soybeans; Macrophomina phaseolina (synonym phaseoli) (root rot and sclerotinia); Microsphaera diffusa (powdery mildew); species of Peronospora (Peronospora spp.) (downy mildew), such as P. manshurica; Phakopsora pachyrhizi and P. meibomiae (soybean rust); species of Phialophora, such as P. gregata.Sclerotinia diseases; species of Phomopsis spp., e.g., sclerotinia disease: P. phaseoli (sexual generation: Diaporthe phaseolorum), species of Pythium spp. (damping-off); species of Phytophthora spp. (wilting, root, leaf, fruit and stem rot), e.g., P. megasperma (synonym P. sojae), species of Rhizoctonia spp., e.g., R. solani (root rot and sclerotinia disease); species of Sclerotinia spp. (sclerotinia disease or white mold rot); species of Septoria spp., e.g., S. glycines (brown spot); S. rolfsii (synonym Athelia rolfsii); species of Thielaviopsis spp. (black root rot).

[0127] More preferably, the polymorphs of the compounds of formula (I-A) and (I-B) of the present invention and mixtures thereof are suitable for controlling the following fungal diseases in soybeans and genetically modified soybeans, such as Bt soybeans, as listed above: species of Alternaria (Alternaria spp.) (Alternaria leaf spot); species of Cercospora (Cercospora spp.) (Cercospora leaf spots), such as C. sojina or C. kikuchii; species of Colletotrichum (Colletotrichum spp.) (sexual generation: species of Glomerella (Glomerella spp.)) (anthracnose), such as C. truncatum or C. gloeosporioides; Corynespora cassiicola (leaf spot); species of Diaporthe (Diaporthe spp.), such as D. phaseolorum (damping-off); species of Fusarium (Fusarium spp.) (sexual generation: species of Gibberella (Gibberella spp.)) (wilt, root rot or sclerotinia), such as, respectively, F. tucumaniae and F. brasiliense, which cause sudden death syndrome in soybeans; Macrophomina phaseolina (synonym phaseoli) (root rot and sclerotinia); species of Peronospora (Peronospora spp.) (downy mildew), such as P. manshurica; Phakopsora pachyrhizi and P. meibomiae (soybean rust); species of Phomopsis (Phomopsis spp.), such as sclerotinia: P. phaseoli (sexual generation: Diaporthe phaseolorum); species of Phytophthora (Phytophthora spp.) (wilt, roots, leaves, fruits and stem roots), such as P. megasperma, synonym P.Phytophthora sojae (P. sojae)); species of Rhizoctonia (Rhizoctonia spp.), for example, R. solani (root rot and sclerotinia rot); species of Septoria (Septoria spp.), for example, S. glycines (brown spot).

[0128] The polymorphs of the compounds of formula (I-A) and (I-B) according to the present invention and mixtures thereof are particularly important for controlling phytopathogenic harmful fungi in soybeans and genetically modified soybeans, such as Bt soybeans, as listed above.

[0129] The polymorphs of the compounds of formula (I-A) and (I-B) according to the present invention and mixtures thereof are also, as listed above, in soybeans and genetically modified soybeans, such as Bt soybeans, respectively, Phakopsora pachyrhizi, P. meibomiae (soybean rust), Cercospora sojina, Cercospora kikuchii, Corynospera cassiicula, Colletotrichum truncatum, Sclerotinia sclerotiorum, Microsphaera diffusa, Septoria Glycine, Peronospora manshurica or Diaporthe caulivora (D. phaseolorum var. caulivora) are particularly important for control.

[0130] In a preferred embodiment, the compounds of the following formula (I-A) and (I-B) and mixtures thereof are, as listed above, usable for the following crops and pests: Preferably, the compounds of formula (I-A) and (I-B) and mixtures thereof are suitable for controlling the following fungal diseases in soybean and genetically modified soybean, such as Bt soybean, as listed above: Alternaria spp. (Alternaria leaf spot); Cercospora spp. (Cercospora leaf spots), such as C. sojina or C. kikuchii; Colletotrichum spp. (sexual stage: Glomerella spp.) (anthracnose), such as C. truncatum or C. gloeosporioides; Corynespora cassiicola (leaf spot); Dematophora (sexual stage: Rosellinia) necatrix (root rot and sclerotinia); Diaporthe spp., such as D. phaseolorum (damping-off); Fusarium spp. (sexual stage: Gibberella spp.) (wilt, root rot or sclerotinia), such as F. tucumaniae and F. brasiliense, which each cause sudden death syndrome in soybean; Macrophomina phaseolina (synonym phaseoli) (root rot and sclerotinia); Microsphaera diffusa (powdery mildew); Peronospora spp. (downy mildew), such as P. manshurica; Phakopsora pachyrhizi and P. meibomiae (soybean rust); Phialophora spp., such as P. gregata.Sclerotinia diseases; species of Phomopsis spp., e.g., for sclerotinia diseases: P. phaseoli (sexual generation: Diaporthe phaseolorum), species of Pythium spp. (damping-off); species of Phytophthora spp. (wilt, root, leaf, fruit, and stem rot), e.g., P. megasperma (synonym P. sojae), species of Rhizoctonia spp., e.g., R. solani (root rot and sclerotinia diseases); species of Sclerotinia spp. (sclerotinia disease or white mold rot); species of Septoria spp., e.g., S. glycines (brown spot); S. rolfsii (synonym Athelia rolfsii); species of Thielaviopsis spp. (black root rot).

[0131] More preferably, the compounds of formula (I-A) and (I-B) and mixtures thereof are suitable for controlling the following fungal diseases in soybean and genetically modified soybean, such as Bt soybean, as listed above: species of Alternaria (Alternaria spp.) (Alternaria leaf spot); species of Cercospora (Cercospora spp.) (Cercospora leaf spots), such as C. sojina or C. kikuchii; species of Colletotrichum (Colletotrichum spp.) (sexual generation: species of Glomerella (Glomerella spp.)) (anthracnose), such as C. truncatum or C. gloeosporioides; Corynespora cassiicola (leaf spot); species of Diaporthe (Diaporthe spp.), such as D. phaseolorum (damping-off); species of Fusarium (Fusarium spp.) (sexual generation: species of Gibberella (Gibberella spp.)) (wilt, root rot or sclerotinia), for example, F. tucumaniae and F. brasiliense, each causing sudden death syndrome in soybean; Macrophomina phaseolina (synonym phaseoli) (root rot and sclerotinia); species of Peronospora (Peronospora spp.) (downy mildew), such as P. manshurica; Phakopsora pachyrhizi and P. meibomiae (soybean rust); species of Phomopsis (Phomopsis spp.), such as sclerotinia: P. phaseoli (sexual generation: Diaporthe phaseolorum); species of Phytophthora (Phytophthora spp.) (wilt, root, leaf, fruit and stem rot), such as P. megasperma, synonym P. sojae (species of Rhizoctonia, e.g., R. solani (root rot and sclerotinia rot); species of Septoria, e.g., S. glycines (brown spot).

[0132] The compounds of formula (I-A) and (I-B) and mixtures thereof according to the invention are particularly important for controlling phytopathogenic harmful fungi in soybeans and genetically modified soybeans, e.g., Bt soybeans, as listed above.

[0133] The compounds of formula (I-A) and (I-B) and mixtures thereof according to the invention are also, as listed above, each particularly important for controlling Phakopsora pachyrhizi, P. meibomiae (soybean rust), Cercospora sojina, Cercospora kikuchii, Corynospera cassiicula, Colletotrichum truncatum, Sclerotinia sclerotiorum, Microsphaera diffusa, Septoria glycines, Peronospora manshurica or Diaporthe caulivora (D. phaseolorum var. caulivora) in soybeans and genetically modified soybeans, e.g., Bt soybeans.

[0134] Polymorphs of the compounds of formula (I-A) or (I-B) according to the invention can be used, for example, in ornamental plants such as lawns, flowers, shrubs, broad-leaved trees or conifers such as evergreens, and also for trunk injection, pest management, etc.

[0135] Within the scope of the present invention, the target crops and / or useful plants to be protected typically include, for example, soft fruit plants such as blackberry, blueberry, cranberry, raspberry, and strawberry; cereals such as barley, corn (maize), millet, rye, rice, triticale, sorghum, and wheat; fiber plants such as cotton, flax, hemp, jute, and sisal; agricultural crops such as sugar and fodder beet, coffee, hop, mustard, canola, poppy, sugarcane, sunflower, tea, and tobacco; fruit trees such as apple, apricot, avocado, banana, cherry, citrus, nectarine, peach, pear, and plum; grasses such as bermudagrass, strawberry clover, bentgrass, centipedegrass, goosegrass, ryegrass, tall fescue, and orchardgrass; herbs such as basil, borage, chive, coriander, lavender, lettuce, mint, oregano, parsley, rosemary, sage, and thyme; leguminous plants such as kidney bean, lentil, pea, and soybean; nuts such as almond, cashew, peanut, hazelnut, pecan, pistachio, and walnut; palms such as oil palm; ornamental plants such as flowers, shrubs, and trees; other trees such as cacao, coconut, olive, and rubber; vegetables such as asparagus, eggplant, broccoli, cabbage, carrot, cucumber, garlic, lettuce, pumpkin, melon, okra, onion, pepper, potato, squash, daikon, spinach, and tomato; and perennial and annual crops including, for example, vine plants such as grapevine.

[0136] The term "useful plant" should be understood to also include useful plants that have been rendered tolerant to herbicides such as bromoxynil, or to certain classes of herbicides (e.g., HPPD inhibitors, ALS inhibitors such as primisulfuron, prosulfuron and trifloxysulfuron, EPSPS (5-enol-pyruvyl-shikimate-3-phosphate synthase) inhibitors, GS (glutamine synthetase) inhibitors or PPO (protoporphyrinogen-oxidase) inhibitors, etc.) by conventional breeding or genetic engineering methods. An example of a crop that has been rendered tolerant to imidazolinones such as imazamox by conventional breeding methods (mutation induction) is Clearfield® summer rape (canola). Examples of crops that have been rendered tolerant to herbicides or certain classes of herbicides by genetic engineering methods include glyphosate- and glufosinate-tolerant maize varieties commercially available under the trade names Roundup Ready®, Herculex I* and LibertyLink®.

[0137] The term "useful plant" should be understood to also include useful plants that have been transformed using recombinant DNA technology so as to be capable of synthesizing one or more selectively acting toxins, such as those known from toxin-producing bacteria belonging in particular to the genus Bacillus.

[0138] Examples of such plants are YieldGard® (maize variety expressing the CryIA(b) toxin); YieldGard Rootworm® (maize variety expressing the CryIIIB(b1) toxin); YieldGard Plus® (maize variety expressing the CryIA(b) and CryIIIB(b1) toxins); Starlink* (maize variety expressing the Cry9(c) toxin); Herculex I® (maize variety expressing the CryIF(a2) toxin and the enzyme phosphinothricine N-acetyltransferase (PAT) to confer resistance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety expressing the CryIA(c) toxin); Bollgard I® (cotton variety expressing the CryIA(c) toxin); Bollgard II® (cotton variety expressing the CryIA(c) and CryIIA(b) toxins); VIPCOT* (cotton variety expressing the VIP toxin); NewLeaf® (potato variety expressing the CryIIIA toxin); Nature-Gard® Agrisure® GT Advantage (GA21 glyphosate tolerance trait), Agrisure® CB Advantage (Bt11 European corn borer (CB) trait), Agrisure® RW (Colorado potato beetle trait) and Protecta®.

[0139] The term "crop" should be understood to include crop plants transformed by recombinant DNA technology so as to be capable of synthesizing one or more selectively acting toxins, such as, for example, those known from toxin-producing bacteria belonging to the genus Bacillus in particular.

[0140] Examples of toxins that can be expressed by such transgenic plants include, for example, insecticidal proteins derived from Bacillus cereus or Bacillus popilliae; or insecticidal proteins derived from Bacillus thuringiensis such as delta-endotoxins such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vips) such as Vip1, Vip2, Vip3 or Vip3A; or insecticidal proteins of nematode symbiotic bacteria such as Photorhabdus luminescens, Xenorhabdus nematophilus, for example, a species of Photorhabdus spp. or a species of Xenorhabdus spp.; toxins produced by animals such as scorpion toxin, spider toxin, large wasp toxin and other insect-specific neurotoxins; toxins produced by fungi such as Streptomycete toxins, plant lectins such as pea lectin, barley lectin or pokeweed lectin; agglutinin; protease inhibitors such as trypsin inhibitor, serine protease inhibitor, patatin, cystatin, papain inhibitor; ribosome-inactivating proteins (RIPs) such as ricin, maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidase, ecdysone inhibitor, HMG-COA-reductase, ion channel blockers such as sodium or calcium blockers, larval hormone esterase, diuretic hormone receptor, stilbene synthase, bibenzyl synthase, chitinase and glucanase.

[0141] Furthermore, in the context of the present invention, it should be understood that delta-endotoxins such as, for example, Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vips) such as, for example, Vip1, Vip2, Vip3 or Vip3A, are in particular also hybrid toxins, truncated toxins and modified toxins. Hybrid toxins are recombinantly produced by new combinations of different domains of these proteins (see, for example, WO 2002 / 15701). Truncated toxins such as truncated Cry1Ab are known. In the case of modified toxins, one or more amino acids of the native toxin are replaced. In such amino acid substitutions, preferably a protease recognition sequence that does not occur naturally is inserted into the toxin, for example, in the case of Cry3A055, a cathepsin-G-recognition sequence is inserted into the Cry3A toxin (see WO 2003 / 018810).

[0142] Examples of such toxins or transgenic plants having the ability to synthesize such toxins are disclosed, for example, in EP 0374753, WO 1993 / 07278, WO 1995 / 34656, EP 0427529, EP 0451878 and WO 2003 / 052073.

[0143] Methods for preparing such transgenic plants are generally known to those skilled in the art and are described, for example, in the above-mentioned publications. For CryI-type deoxyribonucleic acid and its preparation, reference is made, for example, to WO 1995 / 34656, EP 0367474, EP 0401979 and WO 1990 / 13651.

[0144] The toxin contained in the transgenic plant confers resistance to harmful insects on the plant. Such insects can be any of the insect taxa, but are particularly commonly found in beetles (Coleoptera), dipterous insects (Diptera) and butterflies (Lepidoptera).

[0145] Transgenic plants containing one or more genes encoding insecticide resistance and expressing one or more toxins are known, and some of them are commercially available. Examples of such plants are YieldGard® (maize variety expressing the Cry1Ab toxin); YieldGard Rootworm® (maize variety expressing the Cry3Bb1 toxin); YieldGard Plus® (maize variety expressing the Cry1Ab and Cry3Bb1 toxins); Starlink® (maize variety expressing the Cry9C toxin); Herculex I® (maize variety expressing the Cry1Fa2 toxin and the enzyme phosphinothricine N-acetyltransferase (PAT) to achieve resistance to the herbicide glufosinate ammonium); NuCOTN 33B® (cotton variety expressing the Cry1Ac toxin); Bollgard I® (cotton variety expressing the Cry1Ac toxin); Bollgard II® (cotton variety expressing the Cry1Ac and Cry2Ab toxins); VIPCOT® (cotton variety expressing the Vip3A and Cry1Ab toxins); NewLeaf® (potato variety expressing the Cry3A toxin); Nature-Gard®, Agrisure® GT Advantage (GA21 glyphosate tolerance trait), Agrisure® CB Advantage (Bt11 European corn borer (CB) trait) and Protecta®.

[0146] Further examples of such transgenic crops are as follows: 1. Genetically engineered maize (Zea mays) designated Bt11, produced by Syngenta Seeds SAS, Chemin de l’Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. The transgenic expression of a truncated Cry1Ab toxin confers resistance to European corn borer (Ostrinia nubilalis) and Sesamia nonagrioides. Bt11 maize also achieves resistance to the herbicide glufosinate ammonium by transgenic expression of the enzyme PAT.

[0147] 2. Genetically engineered maize (Zea mays) designated Bt176, produced by Syngenta Seeds SAS, Chemin de l’Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. The transgenic expression of Cry1Ab toxin confers resistance to European corn borer (Ostrinia nubilalis) and Sesamia nonagrioides. Bt176 maize also achieves resistance to the herbicide glufosinate ammonium by transgenic expression of the enzyme PAT.

[0148] 3. Genetically engineered maize designated MIR604, produced by Syngenta Seeds SAS, Chemin de l’Hobit 27, F-31 790 St. Sauveur, France, registration number C / FR / 96 / 05 / 10. Insect resistance is conferred by the transgenic expression of a modified Cry3A toxin. This toxin is Cry3A055 modified by the insertion of a cathepsin-G-protease recognition sequence. The preparation of such transgenic maize plants is described in WO 2003 / 018810.

[0149] 4. MON863 maize produced by Monsanto Europe S.A., 270 - 272 Avenue de Tervuren, B - 1150 Brussels, Belgium, registration number C / DE / 02 / 9. MON863 expresses the Cry3Bb1 toxin and has resistance to certain Coleoptera insects.

[0150] 5. IPC531 cotton produced by Monsanto Europe S.A., 270 - 272 Avenue de Tervuren, B - 1150 Brussels, Belgium, registration number C / ES / 96 / 02.

[0151] 6. 1507 maize produced by Pioneer Overseas Corporation, Avenue Tedesco, 7 B - 1160 Brussels, Belgium, registration number C / NL / 00 / 10. Maize genetically engineered for the expression of the Cry1F protein, which confers resistance to certain Lepidoptera insects, and the expression of the PAT protein for resistance to the herbicide glufosinate ammonium.

[0152] 7. NK603×MON810 maize produced by Monsanto Europe S.A., 270 - 272 Avenue de Tervuren, B - 1150 Brussels, Belgium, registration number C / GB / 02 / M3 / 03. Consists of a conventional hybrid maize variety by crossing the genetically engineered varieties NK603 and MON810. NK603×MON810 maize transgenically expresses the protein CP4 EPSPS obtained from a strain CP4 of a species of the genus Agrobacterium (Agrobacterium sp.), thereby conferring resistance to the herbicide Roundup® (containing glyphosate), and also transgenically expresses the Cry1Ab toxin obtained from Bacillus thuringiensis subsp. kurstaki, thereby resulting in resistance to certain Lepidoptera including the European corn borer.

[0153] Preferably, the polymorph of the present invention according to the first or second aspect, or the bactericidal and fungicidal composition according to the present invention containing the polymorph, can be used for controlling or preventing phytopathogenic diseases, particularly phytopathogenic fungi (such as Phakopsora pachyrhizi) in soybean plants.

[0154] In particular, for example, it is a transgenic soybean plant that expresses a toxin such as an insecticidal protein such as delta endotoxin (e.g., Cry1Ac (Cry1Ac Bt protein)). Therefore, this includes events MON87701 (disclosed in WO 2009 / 064652), event MON87701×MON89788 (disclosed in WO 2014 / 170327, commercially available as Intacta RR2 PRO (registered trademark) soybean, for example), event MON87751 (disclosed in WO 2014 / 201235), event DAS-44406-6 (commercially available as Enlist E3 (trademark), DAS-44406-6, disclosed in WO 2012 / 075426), or event DAS-81419-2 (described in WO 2013 / 016527, commercially available as Conkesta (trademark) soybean, for example); event DAS-81419-2×DAS-44406-6 (commercially available as Conkesta (trademark) Enlist E3 (trademark) soybean).

[0155] Useful transgenic events in transgenic soybean plants that can be processed according to the present invention include event DAS-44406-6 / pDAB8264.44.06.1 (soybean, herbicide tolerance, disclosed in WO 2012 / 075426); event DAS-81419-2 (described in WO 2013 / 016527 (e.g., aka Conkesta™, Conkesta™ Enlist E3™ soybean, commercially available as DAS-81419-2×DAS-44406-6 soybean); event DAS-14536-7 / pDAB8291.45.36.2 (soybean, herbicide tolerance, disclosed in WO 2012 / 075429); DAS-68416-4 (soybean, herbicide tolerance, ATCC accession number PTA-10442, disclosed in WO 2011 / 066384, WO 2011 / 066360); event DP-305423-1 (soybean, quality mark, disclosed in WO 2008 / 054747, commercially available as, for example, Treus™, Plenish™, Plenish® high oleic soybean); event DP-356043-5 (soybean, herbicide tolerance, deposited as ATCC PTA-8287, disclosed in WO 2008 / 002872, commercially available as, for example, Optimum GAT™); event FG72 (soybean, herbicide tolerance, disclosed in WO 2011 / 063413); event LL27 (soybean, herbicide tolerance, disclosed in WO 2006 / 108674); event LL55 (soybean, herbicide tolerance, disclosed in WO 2006 / 108675); event EE-GM3 / FG72 (soybean, herbicide tolerance) optionally stacked with event EE-GM1 / LL27 or event EE-GM2 / LL55 (disclosed in WO 2011 / 063413); event MON87701 (soybean, insect control, disclosed in WO 2009 / 064652, WO 2014 / 170327); event MON87701×MON89788 (disclosed in WO 2014 / 170327, commercially available as, for example, Intacta RR2 PRO® soybean);Event MON87705 (soybean, improved fatty acid profile, herbicide tolerance, disclosed in International Publication No. WO 2010 / 037016 or U.S. Patent Application Publication No. 20100080887, commercially available, for example, as Vistive Gold™); Event MON87751 (Lepidoptera resistance, ATCC Accession No. PTA-120166, disclosed in International Publication No. WO 2014 / 201235); Event MON87751×MON87701×MON89788×MON87708 (commercially available as Intacta2 Xtend®); Event MON87708 (soybean, herbicide tolerance, disclosed in International Publication No. WO 2011 / 034704, commercially available, for example, as Genuity® Roundup Ready® 2 Xtend®); Event MON87708×MON89788 (soybean, commercially available, for example, as Roundup Ready® 2 Xtend®); Event MON87712 (soybean, yield, disclosed in International Publication No. WO 2012 / 051199); Event MON87754 (soybean, quality characteristics, disclosed in International Publication No. WO 2010 / 024976); Event MON87769 (soybean, quality traits, disclosed in International Publication No. WO 2009 / 102873); Event MON89788 (soybean, herbicide tolerance, disclosed in International Publication No. WO 2006 / 130436, commercially available, for example, as Genuity® Roundup Ready 2 Yield™); Event SYHT0H2 / SYN-000H2-5 (soybean, herbicide tolerance, disclosed in International Publication No. WO 2012 / 082548); Event DAS-21606-3 (soybean, herbicide tolerance, disclosed in International Publication No. WO 2012 / 033794); Event 8264.44.06.1 (soybean, stacked herbicide tolerance, disclosed in International Publication No. WO 2022 / 012075426); Event pDAB8291.45.36.2 (soybean, stacked herbicide tolerance, disclosed in International Publication No. WO 2012 / 075429); Event pDAB8264.42.32.1 (soybean, stacked herbicide tolerance, disclosed in International Publication No. WO 2013 / 010094); Event A2704-12 (glufosinate tolerance, disclosed in International Publication No. WO 2006 / 108647); Event A5547-127 (phosphinothricin tolerance, disclosed in International Publication No. WO 2006 / 108675);Event BPS-CV127-91 (herbicide tolerance, disclosed in International Publication No. WO 2010 / 080829); Event GU262 (phosphinothricin tolerance, described in APHIS regulatory reference US 98-238-01p); Event MON87708×MON89788×A5547-127; G72×A5547-127 (Event code: MST-FGO72-3×ACS-GMOO6-4, commercially available, for example, as Liberty Link™ soybeans), Event MON-04032-6 (Event code: GTS 40-3-2, http: / / www.agbios.com / static / cropdb / LONG-GTS-40-3-2-printer.html, commercially available, for example, as Roundup Ready® soybeans), Event HB4 (Event code IND-00410-5, US Patent Application Publication No. 2022 / 009011, commercially available, for example, as Verdeca HB4 soybeans).;

[0156] Particularly useful transgenic events in transgenic soybean plants that can preferably be processed according to the present invention include event A2704-12 (glufosinate tolerance, disclosed in WO 2006 / 108647, and commercially available, for example, as Liberty Link™ soybeans), event A5547-127 (phosphinothricin tolerance, disclosed in WO 2006 / 108675 and U.S. Patent No. 8,952,142, and commercially available, for example, as Liberty Link™ soybeans; A5547-35 (event code: ACS-GMOO8-6, gene: pat, and commercially available, for example, as Liberty Link™ soybeans), event MON89788 (soybean, herbicide tolerance, disclosed in WO 2006 / 130436, and commercially available, for example, as Genuity® Roundup Ready 2 Yield™); DP-305423-1 (soybean, quality trait, disclosed in WO 2008 / 054747, and commercially available, for example, as Treus™, Plenish™, Plenish® high oleic soybeans); event MON87701 (soybean, insect resistance, disclosed in WO 2009 / 064652); event MON87701×MON89788 (disclosed in WO 2014 / 170327, and commercially available, for example, as Intacta RR2 PRO® soybeans); event MON87705 (soybean, improved fatty acid profile, herbicide tolerance, disclosed in WO 2010 / 037016 or U.S. Patent Application Publication No. 20100080887, and commercially available, for example, as Vistive Gold™); event FG72 (soybean, herbicide tolerance, disclosed in WO 2011 / 063413); event FG72×A5547-127 (and commercially available, for example, as LibertyLink® GT27™); event SYHT0H2 / SYN-000H2-5 (soybean, herbicide tolerance, disclosed in WO 2012 / 082548); event DAS-81419-2 (described in WO 2013 / 016527, and commercially available, for example, as Conkesta™ soybeans;Event DAS-44406-6 (disclosed in International Publication No. WO 2012 / 075426 and commercially available, for example, as Enlist E3™) or Event DAS-81419-2 (described in International Publication No. WO 2013 / 016527 and commercially available, for example, as Conkesta™ soybean); DAS81419-2 × DAS4406 (commercially available, for example, as Conkesta™ Enlist E3™ soybean); Event DP305423 × GTS 40-3-2 (soybean, quality mark, disclosed in International Publication No. WO 2008 / 054747 and commercially available, for example, as Plenish® high oleic soybean); Event DP-356043-5 (soybean, herbicide tolerance, deposited as ATCC PTA-8287, disclosed in International Publication No. WO 2008 / 002872 and commercially available, for example, as Optimum GAT™), Event MON-04032-6 (Event code: GTS 40-3-2, http: / / www.agbios.com / static / cropdb / LONG-GTS-40-3-2-printer.html, commercially available, for example, as Roundup Ready® soybean) may be mentioned.;

[0157] Furthermore, a list of such transgenic events is provided by the Animal and Plant Health Inspection Service (APHIS) of the United States Department of Agriculture (USDA) and can be found on the website at www.aphis.usda.gov.

[0158] Examples of commercially available genetically modified soybean plants that can preferably be processed according to the present invention include those sold or distributed under the trade names Roundup Ready® (RR1), Roundup Ready 2 Xtend®, Roundup Ready 2 Yield®, XtendFlex®, Intacta® Roundup Ready® 2 Pro (Intacta® RR2 PRO), Intacta 2 Xtend®, Vistive® Gold®, Conkesta Enlist E3®, Conkesta E3®, Enlist E3®, Genuity® Roundup Ready 2 Yield®, Genuity® Roundup Ready® 2 Xtend®, herbicide-tolerant soybean lines, Optimum GAT®, Liberty Link® soybeans, Verdeca HB4 soybeans, Treus®, Plenish®, such as plant seeds of commercially available products.

[0159] Transgenic soybean events containing herbicide tolerance genes are, for example, but not limited to, GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21, A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS81419-2, GU262, SYHTOH2, W62, W98, FG72 and CV127.

[0160] According to one embodiment of the present invention, there is provided the use of a compound of formula (I-A) or a polymorph thereof (I-A) for controlling phytopathogenic fungi in a genetically modified soybean plant, wherein said transgenic soybean event containing a herbicide tolerance gene is, for example, but not limited to, GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21, A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS81419-2, GU262, SYHTOH2, W62, W98, FG72 and CV127.

[0161] According to one embodiment of the present invention, there is provided the use of a compound of formula (I-B) or a polymorph thereof (I-B) for controlling phytopathogenic fungi in a genetically modified soybean plant, wherein said transgenic soybean event containing a herbicide tolerance gene is, for example, but not limited to, GTS 40-3-2, MON87705, MON87708, MON87712, MON87769, MON89788, A2704-12, A2704-21, A5547-127, A5547-35, DP356043, DAS44406-6, DAS68416-4, DAS81419-2, GU262, SYHTOH2, W62, W98, FG72 and CV127.

[0162] The polymorph of the present invention according to the first or second aspect or the bactericidal and fungicidal composition according to the present invention containing the polymorph can be used for controlling or preventing phytopathogenic diseases, particularly phytopathogenic fungi (such as Phakopsora pachyrhizi) in soybean plants. In particular, in scientific literature, certain elite soybean plant varieties in which an R-gene stack that confers a certain immunity or resistance to a specific Phakopsora pachyrhizi has been genetically transferred into the plant genome are known. See, for example, "Fighting Asian Soybean Rust", Langenbach C, et al, Front Plant Science 7(797)2016).

[0163] An elite plant is any plant derived from an elite line such that the elite plant is a plant that represents an elite variety. Non-limiting examples of elite soybean varieties commercially available to farmers or soybean breeders include: AG00802, A0868, AG0902, A1923, AG2403, A2824, A3704, A4324, A5404, AG5903, AG6202AG0934; AG1435; AG2031; AG2035; AG2433; AG2733; AG2933; AG3334; AG3832; AG4135; AG4632; AG4934; AG5831; AG6534; and, AG7231 (Asgrow Seeds, Des Moines, Iowa, USA); BPR0144RR, BPR4077NRR and BPR4390NRR (Bio Plant Research, Camp Point, Ill., USA); DKB17-51 and DKB37-51 (DeKalb Genetics, DeKalb, Ill., USA); DP 4546 RR, and DP 7870 RR (Delta&Pine Land Company, Lubbock, Tex., USA); JG 03R501, JG 32R606C ADD and JG 55R503C (JGL Inc., Greencastle, Ind., USA); NKS 13-K2 (NK Division of Syngenta Seeds, Golden Valley, Minnesota, USA); 90M01, 91M30, 92M33, 93M11, 94M30, 95M30, 97B52, P008T22R2; P16T17R2; P22T69R; P25T51R; P34T07R2; P35T58R; P39T67R; P47T36R; P46T21R; and, P56T03R2 (Pioneer Hi-Bred International, Johnston, Iowa, USA); SG4771NRR and SG5161NRR / STS (Soygenetics, LLC, Lafayette, Ind., USA); S00-K5, S11-L2, S28-Y2, S43-B1, S53-A1, S76-L9, S78-G6, S0009-M2; S007-Y4; S04-D3; S14-A6; S20-T6; S21-M7; S26-P3; S28-N6; S30-V6; S35-C3; S36-Y6; S39-C4; S47-K5; S48-D9; S52-Y2; S58-Z4; S67-R6; S73-S8; and, S78-G6 (Syngenta Seeds, Henderson, Ky., USA); Richer (Northstar Seed Ltd. Alberta, CA); 14RD62 (Stine Seed Co. Ia., USA); or, Armor 4744 (Armor Seed, LLC, Ar., USA).

[0164] Therefore, in a further preferred embodiment, the polymorph (I-A) or (I-B) of the invention according to the first or second aspect or the fungicidal and antifungal composition according to the invention comprising said polymorph (I-A) or (I-B) is used for the control of Phakopsora pachyrhizi (including its fungicidal and antifungal resistant strains described below) in elite soybean plant varieties in which an R-gene stack conferring a certain immunity or resistance to specific Phakopsora pachyrhizi has been genetically transferred into the plant genome. By said use, numerous benefits can be envisaged, such as an improvement in biological activity, a favorable or broad range of activities (including susceptible and resistant strains of Phakopsora pachyrhizi), an improvement in the safety profile, an improvement in crop tolerance, synergistic interactions or enhanced properties, an improvement in the onset of action or a longer-lasting residual activity, a reduction in the number of applications and / or the application rate of the compounds and compositions necessary for the effective control of the plant pathogen (Phakopsora pachyrhizi), whereby beneficial resistance management practices become possible, the environmental impact is reduced and the exposure to the operator is reduced.

[0165] Under certain circumstances, the bactericidal and fungicidal composition according to the invention containing a polymorph of formula (I-A) or (I-B) can exhibit a synergistic interaction between the active ingredients when used in the control or prevention of phytopathogenic diseases, in particular phytopathogenic fungi in soybean plants (such as Phakopsora pachyrhizi) (in particular any of the above transgenic soybean plants).

[0166] Exemplary GM traits conferring high ASR resistance include resistance genes encoding resistance proteins as described below: WO 2019 / 103918 (e.g., without being particularly limited thereto, RG-1 (SEQ ID NO: 47) and active variants or fragments thereof; or the R-genes defined by SEQ ID NO: 28, 42, 43, 44, 45 or 46 of WO 2019 / 103918); WO 2021 / 00878 (e.g., Rpp6907 (SEQ ID NO: 1 of WO 2021 / 00878) and active variants or fragments thereof); WO 2021 / 022022 (e.g., TirA or Tir B (SEQ ID NO: 11 or 16, respectively, of WO 2021 / 022022) or active variants or fragments thereof); WO 2021 / 260673 (e.g., without being particularly limited thereto, RG21 and / or RG22 (SEQ ID NO: 1 or 12 of WO 2021 / 260673) or active variants or fragments thereof); WO 2022 / 173659 (e.g., without being particularly limited thereto, RG30 (SEQ ID NO: 5 of WO 2022 / 173659) or active variants or fragments thereof); WO 2022 / 159341 (e.g., without being particularly limited thereto, SEQ ID NO: 1 and 148 of WO 2022 / 159341 or active variants or fragments thereof); WO 2021 / 154632 A1, WO 2021 / 022026, WO 2021 / 022101, US Patent Application Publication No. 2022 / 0135997 (e.g., without being particularly limited thereto, FIT1 (SEQ ID NO: 2 of US Patent Application Publication No. 2022 / 0135997), active variants or fragments thereof or any of the FIT1 paralogs or orthologs disclosed herein (such as SEQ ID NO: 4, 6, 8, 10, 12, 14, 16, 18 or 20 of US Patent Application Publication No. 2022 / 0135997); US Patent No. 10,842,097 (e.g., without being particularly limited thereto, CcRpp1 or active variants or fragments thereof or any other resistance gene disclosed herein); WO 2022 / 140257 (e.g., CcRpp2-R1 and / or CcRpp2-R3 (SEQ ID NO: 2 or 4 of WO 2022 / 140257) or active variants or fragments thereof);The resistance genes disclosed as RG31 (SEQ ID NO: 1, 3, or 4) or RG35 (SEQ ID NO: 2 or 5) in U.S. Provisional Patent Application No. 63 / 481627; and / or, the resistance genes disclosed as RG32 (SEQ ID NO: 1, 3, or 4) or RG34 (SEQ ID NO: 2, 5, 6, or 17) in U.S. Provisional Patent Application No. 63 / 426524 and U.S. Provisional Patent Application No. 63 / 509586 (each of which is incorporated by reference in its entirety).;

[0167] Exemplary native traits that confer high resistance to ASR or to pathogens from the genus Phakopsora, including the species Phakopsora pachyrhizi and Phakopsora meibomiae, include various intervals and loci associated with Rpp1, Rpp1b, Rpp2, Rpp4, Rpp5, Rpp6, and the ASR resistance locus 1-16. Such native traits can be found, for example, in International Publication No. WO 2009 / 079729, U.S. Patent No. 8,759,607, U.S. Patent No. 8,962,914, International Publication No. WO 2008 / 054546, U.S. Patent No. 8,692,054, U.S. Patent No. 9,091,681, International Publication No. WO 2009 / 132089, U.S. Patent No. 8,669,414, U.S. Patent No. 8,796,503, U.S. Patent No. 8,921,645, International Publication No. WO 2010 / 096227, International Publication No. WO 2010 / 009404, International Publication No. WO 2021 / 154632, U.S. Patent Application Publication No. 2023 / 0067451, International Publication No. WO 2021 / 022026, U.S. Patent Application Publication No. 2022 / 0256795, International Publication No. WO 2021 / 022101, U.S. Patent Application Publication No. 2022 / 0338433, International Publication No. WO 2022 / 173659, International Publication No. WO 2010 / 009404, International Publication No. WO 2017 / 222827, U.S. Patent Application Publication No. 2021 / 0024950, International Publication No. WO 2021 / 000878, U.S. Patent Application Publication No. 2022 / 0380796, U.S. Patent Application Publication No. 2023 / 0147114, and International Patent Application No. PCT / US23 / 60373, each of which is incorporated by reference in its entirety.

[0168] Exemplary soybean varieties that confer high resistance to ASR include soybean cultivars TMG7062, TMG7161, and TMG7261.

[0169] Further soybean varieties that confer high resistance to ASR (caused by Phakopsora pachyrhizi) include, for example, but not particularly limited thereto, TMG7368IPRO (disclosed in International Publication No. 2009079729), TMG7062IPRO, TMG7063IPRO, and TMG7061IPRO.

[0170] Further soybean varieties that confer high resistance to ASR (caused by Phakopsora pachyrhizi) include, for example, but not particularly limited thereto, soybeans having Shield Technology such as BRS511 soybeans, BRS531 soybeans, or Soy-BRS539 (conventional soybeans having Shield (registered trademark) and Block (registered trademark) Technologies).

[0171] The polymorph of the present invention according to the first or second aspect or the bactericidal and fungicidal composition according to the present invention containing the polymorph can be used for controlling or preventing phytopathogenic diseases in soybean plants, particularly phytopathogenic fungi (particularly, Phakopsora pachyrhizi).

[0172] Also, to date, no cross-resistance has been observed between the polymorph and the current bactericidal and fungicidal solution used for controlling Phakopsora pachyrhizi.

[0173] In fact, fungicidal and antifungal-resistant strains of Phakopsora pachyrhizi have been reported in the scientific literature, and strains resistant to one or more fungicidal and antifungal agents from each of at least the following fungicidal and antifungal mode-of-action classifications have been observed: sterol demethylation-inhibitors (DMIs), quinone-outside-inhibitors (QoIs), and succinate dehydrogenase inhibitors (SDHIs). For example, see: “Sensitivity of Phakopsora pachyrhizi towards quinone-outside-inhibitors and demethylation-inhibitors, and corresponding resistance mechanisms.” Schmitz HK et al, Pest Manag Sci (2014) 70:378-388; “First detection of a SDH variant with reduced SDHI sensitivity in Phakopsora pachyrhizi” Simoees K et al, J Plant Dis Prot (2018) 125:21-2; “Competitive fitness of Phakopsora pachyrhizi isolates with mutations in the CYP51 and CYTB genes.” Klosowski AC et al, Phytopathology (2016) 106:1278-1284; “Detection of the F129L mutation in the cytochrome b gene in Phakopsora pachyrhizi.” Klosowski AC et al, Pest Manag Sci (2016) 72:1211-1215.

[0174] Therefore, in a preferred embodiment, the polymorph of the invention according to the first or second aspect, or the bactericidal and fungicidal composition according to the invention containing the polymorph, is used for controlling Phakopsora pachyrhizi that is resistant to one or more bactericidal and fungicidal agents from any of the following bactericidal and fungicidal MoA classifications: sterol demethylation-inhibitors (DMI), quinone-external-inhibitors (QoI), and succinate dehydrogenase inhibitors (SDHI).

[0175] The polymorph of the compound of formula (I-A) or (I-B) according to the invention can be used for controlling or preventing phytopathogenic fungi such as Alternaria species in fruits, vegetables and potatoes; Botrytis cinerea in strawberries, tomatoes, sunflowers, cereals, vegetables and grapes; Rhizoctonia solani in potatoes and vegetables; Uncinula necator in grapes; Cladosporium cucumerinum, Didymella bryoniae, Sphaerotheca fuliginea and Glomerella lagenarium in cucurbitaceous plants; Leveillula taurica in cucurbitaceous plants and solanaceous crops; Fusarium spp. in cereals; Leptosphaeria spp. in cereals; and Zymospetoria spp. in cereals.

[0176] As used herein, the term "habitat" means a field in which a plant is growing, or a field in which seeds of a cultivated plant are sown, or a field in which seeds are to be sown in the soil. This includes soil, seeds and seedlings, as well as established vegetation.

[0177] The term "plant" refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, petioles, foliage and fruits.

[0178] The term "plant propagation material" is understood to represent the reproductive parts of plants such as seeds that can be used for their propagation, and vegetative parts such as cuttings or tubers such as potatoes for example. Examples can include seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes and parts of plants. Also included are germinated plants and sprouts that are to be transplanted after germination or after emerging from the soil. These sprouts may be protected by complete or partial treatment by immersion prior to transplantation. Preferably, the "plant propagation material" is understood to represent seeds.

[0179] The polymorphs of the compounds of formula (I-A) or (I-B) according to the present invention can be used in their as-is form or, preferably, together with auxiliaries that are conveniently employed in the formulation art. For this purpose, they can be conveniently formulated in known manner into emulsifiable concentrates, coating pastes, directly sprayable or dilutable solutions or suspensions, diluted emulsions, wettable powders, soluble powders, dusts, granules, and, for example, capsules in polymeric substances. As well as the type of composition, application methods such as spraying, atomizing, dusting, scattering, coating or pouring are selected according to the intended purpose and the circumstances at that time. The composition may also contain stabilizers, defoamers, viscosity regulators, binders or adhesives, and further auxiliaries such as fertilizers, sources of trace elements, or other formulations for obtaining special effects.

[0180] Suitable carriers and auxiliaries for use in agriculture, for example, can be solid or liquid and are substances useful in the formulation art, such as natural or regenerated mineral substances, solvents, dispersants, wetting agents, adhesives, thickeners, binders or fertilizers. Such carriers are described, for example, in WO 97 / 33890.

[0181] A suspension concentrate is an aqueous formulation in which fine solid particles of an active compound are suspended. Such formulations contain anti-settling agents and dispersants, and may further contain wetting agents to enhance activity, as well as anti-foaming agents and crystal growth inhibitors. In use, these concentrates are diluted in water and usually applied by spraying to the area to be treated. The amount of the active ingredient can be in the range of 0.5% to 95% of the concentrate.

[0182] Wettable powders are in the form of fine particles that are easily dispersible in water or other liquid carriers. These particles contain the active ingredient held in a solid matrix. Typical solid matrices include Fuller's earth, kaolin clay, silica, and other hygroscopic organic or inorganic solids. Wettable powders usually contain 5% to 95% of the active ingredient and small amounts of wetting agents, dispersants, or emulsifiers.

[0183] Emulsifiable concentrates are homogeneous liquid compositions that are dispersible in water or other liquids and may consist only of an active compound and a liquid or solid emulsifier, or may contain a liquid carrier such as xylene, high-boiling aromatic naphtha, isophorone, and other non-volatile organic solvents. In use, these concentrates are dispersed in water or other liquids and usually applied by spraying to the area to be treated. The amount of the active ingredient can be in the range of 0.5% to 95% of the concentrate.

[0184] The granular composition contains both extrudates and relatively coarse particles and is usually applied without dilution in the area where treatment is required. Typical carriers for the granular composition include sand, fuller's earth, attapulgite clay, bentonite clay, montmorillonite clay, vermiculite, perlite, calcium carbonate, brick, pumice, phyllosilicate, kaolin, dolomite, calcined gypsum, wood flour, ground corn cobs, ground peanut hulls, sugar, sodium chloride, sodium sulfate, sodium silicate, sodium borate, magnesia, mica, iron oxide, zinc oxide, titanium oxide, antimony oxide, cryolite, gypsum, diatomaceous earth, calcium sulfate, and other organic or inorganic materials that can absorb the active compound or be coated with the active compound. The granular composition usually contains 5% - 25% active ingredient, which may include surfactants such as high-boiling aromatic naphtha, kerosene, and other petroleum fractions, or vegetable oils; and / or spreading agents such as dextrin, glue, or synthetic resins.

[0185] The powder is a free-flowing admixture of the active ingredient and fine solids such as talc, clay, powders, and other organic and inorganic solids that act as dispersants and carriers.

[0186] The active ingredient (the compound of formula (I-A) or (I-B) and its mixture with component (B)) can be contained in microcapsules. The microcapsules contain the active ingredient in a porous carrier. Thereby, it is possible to release the active ingredient into the environment in a controlled amount (for example, sustained release). The microcapsules usually have a diameter of 0.1 to 500 microns. They contain the active ingredient in an amount of about 25 to 95% by weight of the capsule weight. The active ingredient can be in the form of a solid mass, fine particles in a solid or liquid dispersion, or a suitable solution. The encapsulating membrane can include, for example, natural or synthetic rubber, cellulose, styrene / butadiene copolymer, polyacrylonitrile, polyacrylate, polyester, polyamide, polyurethane, polyurea, or chemically modified polymers and xanthan gum starch or other polymers known to those skilled in the art. Alternatively, extremely fine microcapsules can be formed by containing the active ingredient in the form of fine particles in a solid matrix of the base, but the microcapsules themselves are not encapsulated.

[0187] Microcapsules are typically small droplets or granules of an active ingredient encapsulated within an inert, porous shell that is capable of releasing the encapsulated material to the surroundings at a controlled rate. The encapsulated droplets typically have a diameter of 1 to 50 microns. The encapsulated liquid typically constitutes 50 to 95% of the weight of the capsule and may contain a solvent in addition to the active compound. Encapsulated granules are generally porous granules having a porous membrane that seals the pore openings of the granules and retains the active species in liquid form within the pores of the granules. The granules typically range in diameter from 1 millimeter to 1 centimeter, preferably from 1 to 2 millimeters. The granules are formed by extrusion, agglomeration or prilling, or are natural. Examples of such materials are vermiculite, fired clay, kaolin, attapulgite clay, sawdust and granular carbon. Shell or membrane materials include natural and synthetic rubbers, cellulosic materials, styrene-butadiene copolymers, polyacrylonitrile, polyacrylate, polyester, polyamide, polyurethane and starch xanthate.

[0188] Other useful formulations for agrochemical applications include simple solutions of the active ingredient in a solvent such as acetone, alkylated naphthalene, xylene and other organic solvents in which complete dissolution at the desired concentration is achieved. Pressurized sprayers in which the active ingredient is sprayed in a finely divided form as the low-boiling dispersant solvent carrier evaporates may also be used.

[0189] Suitable agricultural adjuvants and carriers useful in formulating the compositions of the invention of the above formulation types are well known to those skilled in the art.

[0190] Possible liquid carriers include, for example, water, toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone, amyl acetate, 2-butanone, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetate, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol abietate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethylformamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, diproxitol, alkyl pyrrolidinone, ethyl acetate, 2-ethylhexanol, ethylene carbonate, 1,1,1-Trichloroethane, 2-heptanone, α-pinene, d-limonene, ethylene glycol, ethylene glycol butyl ether, ethylene glycol methyl ether, γ-butyrolactone, glycerol, glycerol diacetate, glycerol monoacetate, glycerol triacetate, hexadecane, hexylene glycol, isoamyl acetate, isobornyl acetate, isooctane, isophorone, isopropylbenzene, isopropyl myristate, lactic acid, laurylamine, mesityloxide, methoxy-propanol, methyl isoamyl ketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyl oleate, methylene chloride, m-xylene, n-hexane, n-octylamine, octadecanoic acid, octylamine acetate, oleic acid, oleylamine, o-xylene, phenol, polyethylene glycol (PEG400), propionic acid, propylene glycol, propylene glycol monomethyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylene sulfonic acid, paraffin, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, methanol, ethanol, isopropanol, and high molecular weight alcohols such as amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol, etc., ethylene glycol, propylene glycol, glycerin and N-methyl-2-pyrrolidone are mentioned. For dilution of the concentrate, water is a generally selected carrier.,

[0191] Suitable solid carriers include, for example, talc, titanium dioxide, phyllosilicate clay, silica, attapulgite clay, kieselguhr, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, fuller's earth, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell powder and lignin.

[0192] A wide range of surfactants are advantageously utilized in both the liquid and solid compositions, such as those designed to be diluted with a carrier prior to application. These surfactants typically contain formulations of 0.1% to 15% by weight when in use. They can be anionic, cationic, nonionic, or polymeric in nature and can be utilized as emulsifiers, wetting agents, suspending agents, or for other purposes. Typical surfactants include alkyl sulfates such as ammonium lauryl sulfate diethanolamine; alkylaryl sulfonate salts such as calcium dodecylbenzene sulfonate; alkylphenol-alkylene oxide adduct products such as nonylphenol-C.sub.18 ethoxylate; alcohol-alkylene oxide adduct products such as tridecyl alcohol-C.sub.16 ethoxylate; soaps such as sodium stearate; alkylnaphthalene sulfonate salts such as sodium dibutylnaphthalene sulfonate; dialkyl esters of sulfosuccinates such as sodium di(2-ethylhexyl) sulfosuccinate; sorbitol esters such as sorbitol oleate; quaternary amines such as lauryl trimethyl ammonium chloride; polyethylene glycol esters of fatty acids such as polyethylene glycol stearate; block copolymers of ethylene oxide and propylene oxide; and salts of mono- and dialkyl phosphate esters.

[0193] Other adjuvants commonly utilized in agricultural compositions include crystallization inhibitors, viscosity modifiers, suspending agents, spray particle regulators, pigments, antioxidants, foaming agents, defoaming agents, light blockers, solubilizers, defoaming agents, sequestering agents, neutralizing agents and buffers, corrosion inhibitors, dyes, odorants, spreading agents, penetration aids, trace elements, emollients, lubricants, and fixing agents.

[0194] Furthermore, other biocidal active ingredients or compositions may be combined with the composition of the present invention, used in the method of the present invention, and applied simultaneously or sequentially with the composition of the present invention. When applied simultaneously, these further active ingredients may be formulated together with the composition of the present invention or, for example, mixed together in a spray tank. These further biocidal active ingredients may be fungicides, herbicides, insecticides, bactericides, acaricides, nematicides and / or plant growth regulators.

[0195] Pesticides are referred to herein using their common names, which are known, for example, from “The Pesticide Manual”, 15th Ed., British Crop Protection Council 2009.

[0196] In addition, the composition of the present invention may also be applied together with one or more systemic acquired resistance inducers (“SAR” inducers). SAR inducers are known and are described, for example, in U.S. Patent No. 6,919,298 and include, for example, salicylates and the commercially available SAR inducer acibenzolar-S-methyl.

[0197] Polymorphs of the compounds of formula (I-A) or (I-B) according to the present invention are usually used in the form of agrochemical compositions and can be applied to the crop area or plants to be treated simultaneously or sequentially with further compounds. These further compounds can be, for example, fertilizers or trace element donors, or other preparations that affect plant growth. They can also be selective or non-selective herbicides, as well as insecticides, fungicides, bactericides, nematicides, molluscicides, or mixtures of several of these preparations, optionally with further carriers, surfactants or application-promoting adjuvants customarily used in the field of formulations.

[0198] The polymorphs of the compounds of formula (I-A) or (I-B) according to the present invention can be used in the form of a (fungicidal and fungistatic) composition containing the polymorphs defined herein as the active ingredient in free form or in a salt form usable as an agrochemical, together with at least one of the above adjuvants, for the control or protection against phytopathogenic microorganisms.

[0199] The present invention thus provides a composition, preferably a fungicidal and fungistatic composition, comprising a polymorph of a compound of formula (I-A) or (I-B) according to the present invention, an agriculturally acceptable carrier, and optionally an adjuvant. The agriculturally acceptable carrier is, for example, a carrier suitable for agricultural use. Agricultural carriers are well known in the art. Preferably, the composition may contain at least one or more pest control active compounds, for example additional fungicidal and fungistatic active ingredients, in addition to the polymorph of the compound of formula (I-A) or (I-B).

[0200] The polymorph of the compound of formula (I-A) or (I-B) according to the present invention may be the sole active ingredient in the composition, or may be mixed with one or more additional active ingredients such as a pest control agent, a fungicidal and fungistatic agent, a synergist, a herbicide or a plant growth regulator, where appropriate. The additional active ingredients may, in some cases, result in unexpected synergistic activity.

[0201] Examples of suitable additional active ingredients include the following acyl amino acid fungicides and bactericides, aliphatic nitrogen fungicides and bactericides, amide fungicides and bactericides, anilide fungicides and bactericides, antibiotic fungicides and bactericides, aromatic fungicides and bactericides, arsenic fungicides and bactericides, aryl phenyl ketone fungicides and bactericides, benzamide fungicides and bactericides, benzanilide fungicides and bactericides, benzimidazole fungicides and bactericides, benzothiazole fungicides and bactericides, botanical fungicides and bactericides, cross-linked diphenyl fungicides and bactericides, carbamate fungicides and bactericides, carbanylate fungicides and bactericides, conazole fungicides and bactericides, copper fungicides and bactericides, dicarboximide fungicides and bactericides, dinitrophenol fungicides and bactericides, dithiocarbamate fungicides and bactericides, dithiolane fungicides and bactericides, flamide fungicides and bactericides, flanilide fungicides and bactericides, hydrazide fungicides and bactericides, imidazole fungicides and bactericides, mercury fungicides and bactericides, morpholine fungicides and bactericides, organophosphorus fungicides and bactericides, organotin fungicides and bactericides, oxathiine fungicides and bactericides, oxazole fungicides and bactericides, phenylsulfamide fungicides and bactericides, polysulfide fungicides and bactericides, pyrazole fungicides and bactericides, pyridine fungicides and bactericides, pyrimidine fungicides and bactericides, pyrrole fungicides and bactericides, quaternary ammonium fungicides and bactericides, quinoline fungicides and bactericides, quinone fungicides and bactericides, quinoxaline fungicides and bactericides, strobilurin fungicides and bactericides, sulfonanilide fungicides and bactericides, thiadiazole fungicides and bactericides, thiazole fungicides and bactericides, thiazolidine fungicides and bactericides, thiocarbamate fungicides and bactericides, thiophene fungicides and bactericides, triazine fungicides and bactericides, triazole fungicides and bactericides, triazolopyrimidine fungicides and bactericides, urea fungicides and bactericides, valine amide fungicides and bactericides, and zinc fungicides and bactericides.

[0202] Examples of suitable additional active ingredients include the following: petroleum, 1,1-bis(4-chlorophenyl)-2-ethoxyethanol, 2,4-dichlorophenylbenzenesulfonate, 2-fluoro-N-methyl-N-1-cinnamaldehyde, 4-chlorophenylphenylsulfone, acetoprole, aldoxycarb, amidithion, amidithioate, amiton, hydrogen oxalate amiton, amitraz, aramite, arsenic trioxide, azobenzene, azothoate, benomyl, benoxaphos, benzyl benzoate, bixafen, brofenvalerate, bromocyclene, bromophos, bromopropylate, buprofezin, butocarboxim, butoxycarboxim, butylpyridaben, calcium polysulfide, camphorophenicol, carbaryl, carbophenothion, cymiazole, chinomethionat, chlorbenside, chlordimeform, chlordimeform hydrochloride, chlorphenethol, chlorphensone, chlorphen sulfide, chlorobenzilate, chloromethiuron, chloropropylate, chlorothiophos, cinerin I, cinerin II, cinerin s, chrysanthemum, coumaphos, chlorotoluron, chlorotoxyfos, kufraeb, cyanthoate, DCPM, DDT, demephion, demephion-O, demephion-S, demeton-methyl, demeton-O, demeton-O-methyl, demeton-S, demeton-S-methyl, demeton-S-methyl sulfone, dichlofluanid, dichlorvos, dicriphos, dienochlor, dimefox, dinex, dinex dicrexine, dinocap-4, dinocap-6, dinocron, dinopenton, dinosulfon, dinoterbon, dioxathion, diphenyl sulfone, disulfiram, DNOC, dofenapyn, doramectin, endothion, eprinomectin, ethioate methyl, ethirimol, fenazaflor, fenbutatin oxide, phenothiocarb, fenpyrazamine, fenpyroximate, fenpyrad, fenson, fentrifanil, flubenzimine, flucycloxuron, fluenethiou, fluorbenside, FMC1137, formetanate, formetanate hydrochloride, formparanate, γ-HCH, gliotoxin, halfenprox, hexadecyl cyclopropanecarboxylate, isocarbophos, jasmonin I,Jasmolin II, Jodfenphos, Lindane, Malonoben, Mecarbam, Methidathion, Mesulfen, Methacrifos, Methyl bromide, Methomyl, Mexacarbate, Milbemycin oxime, Mipafox, Monocrotophos, Morphothion, Moxidectin, Naled, 4-Chloro-2-(2-chloro-2-methyl-propyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazin-3-one, Nifluridide, Nikkomycin, Nitrilacarb, Nitrilacarb 1:1 zinc chloride complex, Omethoate, Oxydeprofos, Oxydisulfoton, pp’-DDT, Parathion, Permethrin, Fenchlorphos, Phosalone, Phosphorothioate, Phosphamidon, Polychloroterpene, Polynactin, Proclonol, Promacyl, Propoxur, Prothidathion, Prothoate, Pyrethrin I, Pyrethrin II, Pyrethrin, Pyridafenthion, Pyrimidate, Quinalphos, Quincholphos, R-1492, Phosphoglycine, Rotenone, Schradan, Cephos, Selamectin, Sofamide, SSI-121, Sulfiram, Sulfuryl fluoride, Sulfotepp, Sulfur, Diflubenzuron, τ-Fluvalinate, TEPP, Terbumethrin, Tetradifon, Tetrasul, Thiafenthox, Thiocarboxime, Thiofanox, Thimet, Thioquinox, Tsurugiensin, Triamiphos, Triarathene, Triazophos, Triazolone, Triphenyl phosphate, Trinactin, Bamidothion, Vaniliprole, Vetoxazine, Copper neodecanoate, Copper sulfate, Sibutramine, Dicloran, Dichlorophen, Endothal, Fentin, Hydrated lime, Nabam, Quinoclamine, Quinone amide, Simazine, Triphenyltin acetate, Triphenyltin hydroxide, Crufomate, Piperazine, Thiophanate, Chloralose, Fenthion, Pyridin-4-amine, Strychnine, 1-Hydroxy-1H-pyridine-2-thione, 4-(Quinoxalin-2-ylamino)benzenesulfonamide, 8-Hydroxyquinoline sulfate, Bronopol, Copper hydroxide, Cresol, Dipyrithione, Dodine, Fenaminosulf, Formaldehyde, Hydralazine, Kasugamycin, Kasugamycin hydrochloride hydrate, Nickel bis(dimethyldithiocarbamate), Nitrapyrin, Octhilinone, Oxolinic acid, Oxytetracycline, Potassium hydroxyquinoline sulfate,Probenazole, Streptomycin, Streptomycin sesquisulfate, Techlofthalam, Thimerosal, Adoxophyes orana GV, Agrobacterium radiobacter, Amblyseius spp., Anagrapha falcifera NPV, Anagrus atomus, Aphelinus abdominalis, Aphidius colemani, Aphidoletes aphidimyza, Autographa californica NPV, Bacillus sphaericus Neide, Beauveria brongniartii, Chrysoperla carnea, Cryptolaemus montrouzieri, Cydia pomonella GV, Dacnusa sibirica, Diglyphus isaea, Encarsia formosa, Eretmocerus eremicus, Heterorhabditis bacteriophora and H. megidis, Hippodamia convergens, Leptomastix dactylopii, Macrolophus caliginosus, Mamestra brassicae NPV, Metaphycus helvolus, Metarhizium anisopliae var. acridum, Metarhizium anisopliae var. anisopliaeNeodiprion sertifer NPV and N. lecontei NPV, species of the genus Orius Paecilomyces fumosoroseus, Phytoseiulus persimilis, Steinernema bibionis, Steinernema carpocapsae, Steinernema feltiae, Steinernema glaseri, Steinernema riobrave b, Steinernema riobravis, Steinernema scapterisci, Steinernema spp., Trichogramma spp., Typhlodromus occidentalis, Verticillium lecanii, apholate, bisazir, busulfan, dimatif, hemer, hempa, metepa, methiotepa, methyl apholate, moldid, penfluron, tepa, thiohempa, thiotepa, tretamine, uredepa, (E)-deca-5-en-1-yl acetate + (E)-deca-5-en-1-ol, (E)-trideca-4-en-1-yl acetate, (E)-6-methylhepta-2-en-4-ol, (E,Z)-tetradeca-4,10-dien-1-yl acetate, (Z)-dodeca-7-en-1-yl acetate, (Z)-hexadeca-11-enal, (Z)-hexadeca-11-en-1-yl acetate, (Z)-hexadeca-13-en-11-in-1-yl acetate, (Z)-icos-13-en-10-one, (Z)-tetradeca-7-en-1-al, (Z)-tetradeca-9-en-1-ol, (Z)-tetradeca-9-en-1-yl acetate, (7E,9Z)-dodeca-7,9-dien-1-yl acetate, (9Z,11E)-tetradeca-9,11-dien-1-yl acetate, (9Z,12E)-tetradeca-9,12-dien-1-yl acetate, 14-methyloctadeca-1-ene,4-Methylnonan-5-ol + 4-Methylnonan-5-one, α-Multistriatin, Brevicomin, Codlelure, Codlemone, Querelure, Disparlure, Dodeca-8-en-1-yl acetate, Dodeca-9-en-1-yl acetate, Dodeca-8,10-dien-1-yl acetate, Dominicalure, Ethyl 4-methyloctanoate, Eugenol, Frontalin, Grandlure, Grandlure I, Grandlure II, Grandlure III, Grandlure IV, Hexalure, Ipsdienol, Ipsenol, Japonilure, Linalool, Litlure, Looplure, Medlure, Megatomonic acid, Methyleugenol, Muscalure, Octadeca-2,13-dien-1-yl acetate, Octadeca-3,13-dien-1-yl acetate, Orfluralure, Oricolure, Ostramone, Siglure, Soldiure, Sulcatol, Tetradeca-11-en-1-yl acetate, Trimedlure, Trimedlure A, Trimedlure B1, Trimedlure B2, Trimedlure C, Trunc-call, 2-(Octylthio)ethanol, Butapironoxyl, Butoxy(polypropylene glycol), Dibutyl adipate, Dibutyl phthalate, Dibutyl succinate, Diethyltoluamide, Dimethyl carbonate, Dimethyl phthalate, Ethylhexanediol, Hexamide, Methokin-butyl, Methyl neodecanamide, Oxamate, Picaridin, 1-Dichloro-1-nitroethane, 1,1-Dichloro-2,2-bis(4-ethylphenyl)ethane, 1,2-Dichloropropane + 1,3-Dichloropropene, 1-Bromo-2-chloroethane, 2,2,2-Trichloro-1-(3,4-dichlorophenyl)ethyl acetate, 2,2-Dichlorovinyl 2-ethylsulfinylethyl methyl phosphate, 2-(1,3-Dithiolan-2-yl)phenyl dimethylcarbamate, 2-(2-Butoxyethoxy)ethyl thiocyanate, 2-(4,5-Dimethyl-1,3-dioxolan-2-yl)phenyl methylcarbamate, 2-(4-Chloro-3,5-xylyloxy)ethanol, 2-Chlorovinyl diethyl phosphate, 2-Imidazolidone, 2-Isovalerylindane-1,3-dione, 2-Methyl(prop-2-ynyl)aminophenyl methylcarbamate, 2-Thiocyanatoethyl laurate,3-Bromo-1-chloroprop-1-ene, 3-methyl-1-phenylpyrazol-5-yl dimethylcarbamate, 4-methyl(prop-2-ynyl)amino-3,5-xylyl methylcarbamate, 5,5-dimethyl-3-oxocyclohex-1-enyl dimethylcarbamate, acetion, acrylonitrile, aldrin, aloxamidine, alicarb, α-ecdysone, aluminium phosphide, aminocarb, anabasine, atidathion, azamethiphos, Bacillus thuringiensis δ-endotoxin, barium hexafluorosilicate, barium polysulphide, barthrin, Bayer 22 / 190, Bayer 22408, β-cyfluthrin, β-cyphenothrin, bioethanomethrin, biopermethrin, bis(2-chloroethyl) ether, sodium borate, bromfenvinfos, bromo-DDT, bufencarb, butacarb, butathiofos, butonate, calcium arsenate, calcium cyanide, carbon disulphide, carbon tetrachloride, cartap hydrochloride, sevin, chlorbicyclen, chlordane, chlordecone, chloroform, chloropicrin, chloroxime, chlorprozophos, cis-resmethrin, cispermethrin, chlorthrin, copper acetoarsenite, copper arsenate, copper oleate, cumithoate, cryolite, CS708, cyanofenphos, cyanophos, cycloprothrin, cythioate, d-tetramethrin, DAEP, dazomet, decarbofuran, diamidafos, dicapthon, dichlorophenthion, dicresyl, diclornil, dieldrin, diethyl 5-methylpyrazol-3-yl phosphate, dicrotophos, dimefluthrin, dimethan, dimenthrin, dimethylvinphos, dimethyland, dinopropr, dinosam, dinoseb, diofenolan, dioxabenzofos, dichlorvos, DSP, ecdysterone, EI 1642, EMPC, EPBP, ethion, ethiofencarb, ethyl formate, ethylene dibromide, dichloroethane, ethylene oxide, EXD, fenchlorphos, fenethacarb, fenitrothion, phenoxycarb, fenpyrothrin, fenthion-ethyl, flucofuron, formothion, fosmethilan, fosfirat, fosthietan, flathiacarb, flumethrin, guazatine, guazatine acetate,Sodium tetrathiocarboxylate, halfenprox, HCH, HEOD, heptachlor, heterophos, HHDN, hydrogen cyanide, hikindarb, IPSP, isazophos, isobenzan, isodrin, isofenphos, isolan, isoprothiolane, isoxathion, juvenile hormone I, juvenile hormone II, juvenile hormone III, kerevan, kinoprene, lead arsenate, leptophos, lirimfos, lithidathion, m-cumenyl methylcarbamate, magnesium phosphide, madex, mecarbofos, menazon, mercurous chloride, mesulfenfos, metam, metam-potassium, metam-sodium, methanesulfonyl fluoride, methocrotophos, methoprene, methothrin, methoxychlor, methyl isothiocyanate, methyl chloroform, methylene chloride, methoxadiazone, mirex, naphthalophos, naphthalene, NC-170, nicotine, nicotine sulfate, nithiazine, nor-nicotine, O-5-dichloro-4-iodophenyl O-ethyl ethylphosphonothioate, O,O-diethyl O-4-methyl-2-oxo-2H-chromen-7-yl phosphorothionate, O,O-diethyl O-6-methyl-2-propylpyrimidin-4-yl phosphorothionate, O,O,O’,O’-tetrapropyl dithiopyrophosphate, oleic acid, para-dichlorobenzene, parathion-methyl, pentachlorophenol, pentachlorophenyl laurate, PH60-38, fencapton, phosphonicochlor, phosphine, hokxim-methyl, pirimiphos, polychlorodicyclopentadiene isomer, potassium arsenite, potassium thiocyanate, precocene I, precocene II, precocene III, pyrimidophos, profluthrin, promecarb, prothiofos, pyrazophos, pyresmethrin, cassia, quinalphos-methyl, quinothion, rafoxanide, resmethrin, rotenone, cadethrin, ryania, ryanodine, sabadilla, schradan, sebufos, SI-0009, thiapronyl, sodium arsenite, sodium cyanide, sodium fluoride, sodium hexafluorosilicate, sodium pentachlorophenoxide salt, sodium selenate, sodium thiocyanate, sulcofuron, sulcofuron-sodium, sulfuryl fluoride, sulprofos, tar oil, thionazin, TDE, tebupirimfos, temephos, terallethrin,tetrachloroethane, chlorophos, thiocyclam, thiocyclam hydrogen oxalate, thionazin, thiosultap, thiosultap-sodium, tralomethrin, transpermethrin, triazamate, trichlorometaphos-3, trichloronate, trimethacarb, tolprocarb, triclopyricarb, triprene, veratridine, veratrin, XMC, zeta-methrin, zinc phosphide, zolaprofos, metofluthrin, tetramethylfluthrin, bis(tributyltin) oxide, bromoacetamide, ferric phosphate, niclosamide-olamine, tributyltin oxide, pyrimorph, trifenmorph, 1,2-dibromo-3-chloropropane, 1,3-dichloropropene, 3,4-dichlorotetrahydrothiophene 1,1-dioxide, 3-(4-chlorophenyl)-5-methylrhodanine, 5-methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid, 6-isopentenylaminopurine, anisoflutopurine, benclothiaz, cytokinin, DCIP, lufural, isamidophos, kinetin, Myrothecium verrucaria composition, tetrachlorothiophene, xylenol, zeatin, potassium ethylxanthate, acibenzolar, acibenzolar-S-methyl, Reynoutria sachalinensis extract, α-chlorohydrin, ants, barium carbonate, bistiosem, brodifacoum, bromadiolone, bromethalin, chlorophacinone, cholecalciferol, coumachlor, coumafuryl, coumatetralyl, crimidine, diphenacoum, diphthialone, difacinone, ergocalciferol, flocoumafen, fluoroacetamide, flupropazone, flupropazone hydrochloride, norbormide, phosphacetheum, phosphorus, pindone, pyrinuron, silymarin, sodium fluoroacetate, potassium sulfate, warfarin, 2-(2-butoxyethoxy)ethyl piperonate, 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone, farnesol + nerolidol, verbascine, MGK 264, piperonyl butoxide, piprotal, propyl isomer, S421, sesamex, sesasmolin, sulfoxide, anthraquinone, copper naphthenate, copper oxychloride, sulfur,Dicyclopentadiene, thiram, zinc naphthenate, dithiram, imanin, ribavirin, chloroinconazide, mercury(II) oxide, thiophanate-methyl, azaconazole, bitertanol, bromoconazole, cyproconazole, difenoconazole, diniconazole, epoxyconazole, fenbuconazole, Flucinoconazole, Flusilazole, Flutriafol, Flutolanil, Hexaconazole, Imazalil, Imibenconazole, Ipconazole, Metconazole, Myclobutanil, Paclobutrazol, Pefurazoate, Penconazole, Prothioconazole, Pyriofenox, Prochloraz, Propiconazole, Pyrisoxazole, Cymoxanil, Tebuconazole, Tetraconazole, Triadimefon, Triadimenol, Triflumizole, Triticonazole, Ancymidol, Fenarimol, Nuarimol, Bupirimate, Dimethirimol, Ethirimol, Dodemorph, Fenpropimorph, Spiroxamine, Tridemorph, Cyprodinil, Mepanipyrim, Pyrimethanil, Fenpiclonil, Fluazinam, Benalaxyl, Furalaxyl, Metalaxyl, R-Metalaxyl, Ofurace, Oxadixyl, Carbendazim, Diethofencarb, Fuberidazole, Thiabendazole, Chlorothalonil, Dichlozoline, Microclozine, Procymidone, Vinclozolin, Boscalid, Carboxin, Fenfluram, Flutolanil, Mepronil, Oxathiapiprolin, Penthiopyrad, Tifluzamide, Dodine, Iminoctadine, Azoxystrobin, Dimoxystrobin, Enestroburin, Fenaminstrobin, Fluopicoxystrobin, Fluoxastrobin, Kresoxim-methyl, Metominostrobin, Trifloxystrobin, Orysastrobin, Picoxystrobin, Pyraclostrobin, Pyrametostrobin, Pyraoxystrobin, Ferbam, Mancozeb, Maneb, Thiram, Propineb, Zineb, Captan, Captan, Fluoroimide, Folpet, Trifluamide, Bordeaux mixture, Copper oxide, Mancozeb, Copper oxychloride, Nitrothalisopropyl, Edifenphos, Iprobenfos, Phosphodifen, Tolclofos-methyl, Anilazine, Benalaxyl-M, Blasticidin-S, Chloroneb, Chlorothalonil, Ciflufenamid, Simoxanil, Cyclobutrifluram, Diclocymet, Diclofluanid, Dichloran, Diethofencarb, Dimethomorph, Flumorph, Dithianon, Ethaboxam, Ethirimol, Famoxadone, Fenamidone, Phenoxanil, Ferimzone, Fluazinamflumetylsulforim, fluopicolide, fluoxastrobin, flusulfamide, fluxapyroxad, fenhexamid, fosetyl-aluminum, hymexazol, iprovalicarb, cyazofamid, methiocarb, metrafenone, penthiopyrad, phthalide, polyoxin, propamocarb, pyribencarb, proquinazid, pyroquilon, pyrifluquinazon, quinoxyfen, quintozene, thiazinyl, triazoxide, tricyclazole, trifloxystrobin, validamycin, valifenalate, zoxamide, mandipropamid, flubenthram, isopyrazam, sedaxane, benzovindiflupyr, pidiflumetofen, 2,4-D (2,4-dichlorophenoxyacetic acid), 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3’,4’,5’-trifluoro-biphenyl-2-yl)-amide, isoflupyrasulfuron, isothianil, diphenamid, 6-ethyl-5,7-dioxo-pyrrolo[4,5][1,4]dithieno[1,2-c]isothiazole-3-carbonitrile, 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide, 4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine-3-carbonitrile, (R)-3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-2,5-dimethyl-pyrazol-3-amine, 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, fluindapyr, kresoxim-methyl (jiaxiangjunzhi), lvbenmixianan, diclobentiazox, mandestrobin, 3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1-yl)quinolone, 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phenyl]propan-2-ol, oxathiapiprolin,tert-Butyl N-[6-[[[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate, pyraclofamid, imiproflam, turorolcarb, mefenoxazol, ipfentrioxazol, 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide, N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methyl-formamidine, N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethylphenyl]-N-ethyl-N-methyl-formamidine, [2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]thiazol-4-yl]-4,5-dihydroisoxazol-5-yl]-3-chloro-phenyl]methanesulfonic acid, but-3-ynyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate, methyl N-[[5-[4-(2,4-dimethylphenyl)triazol-2-yl]-2-methylphenyl]methyl]carbamate, 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine, pyridachlometyl, 3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide, 1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methylphenyl]-4-methyltetrazol-5-one, 1-methyl-4-[3-methyl-2-[[2-methyl-4-(3,4,5-trimethylpyrazol-1-yl)phenoxy]methyl]phenyl]tetrazol-5-one, aminopyrifen, ametoctradin, amisulbrom, penflufen, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-penta-3-enamide, fluripicoxamid, fenpicoxamid, metaripicoxamid, tebufloquin, iprobufenoxine, quinofumelin, isophentamide,Ethyl 1-[[4-[[2-(trifluoromethyl)-1,3-dioxolan-2-yl]methoxy]phenyl]methyl]pyrazole-3-carboxylate (which can be prepared from the method described in International Publication No. WO2020 / 056090), ethyl 1-[[4-[(Z)-2-ethoxy-3,3,3-trifluoro-prop-1-enoxy]phenyl]methyl]pyrazole-3-carboxylate (which can be prepared from the method described in International Publication No. WO2020 / 056090), methyl N-[[4-[1-(4-cyclopropyl-2,6-difluoro-phenyl)pyrazol-4-yl]-2-methyl-phenyl]methyl]carbamate (which can be prepared from the method described in International Publication No. WO2020 / 097012), methyl N-[[4-[1-(2,6-difluoro-4-isopropyl-phenyl)pyrazol-4-yl]-2-methyl-phenyl]methyl]carbamate (which can be prepared from the method described in International Publication No. WO2020 / 097012), 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide (which can be prepared from the method described in International Publication No. WO2020 / 109391), 6-chloro-N-[2-(2-chloro-4-methyl-phenyl)-2,2-difluoro-ethyl]-3-(3-cyclopropyl-2-fluoro-phenoxy)-5-methyl-pyridazine-4-carboxamide (which can be prepared from the method described in International Publication No. WO2020 / 109391), 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide (which can be prepared from the method described in International Publication No. WO2020 / 109391), N-[2-[2,4-dichloro-phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide, N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide, benzothiostrobin, fenamacril, zinc salt of 5-amino-1,3,4-thiadiazole-2-thiol (2:1), fluopyram, flufenoxadiazam, flutianil,fluopicolide, pyrapropion, picarbutrazox, 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-inden-4-yl)pyridine-3-carboxamide, 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylinden-4-yl)pyridine-3-carboxamide, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, methyltetraprole, α-(1,1-dimethylethyl)-α-[4’-(trifluoromethoxy)[1,1’-biphenyl]-4-yl]-5-pyrimidinemethanol, fluoxapiprolin, enoxastrobin, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoate, methyl 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1,2,4-triazol-1-ylmethyl)cyclopentanecarboxylate, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-sulfanyl-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, trinexapac-ethyl, kresoxim-methyl, zhongshengmycin, copper thiazole, zinc thiazole, abamectin, iprodione, cebuthrin, thiamethoxam, N’-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine, N’-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine,N’-[5-Bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N’-[5-chloro-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N’-[5-bromo-2-methyl-6-(1-methyl-, 2-Propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidine (these compounds can be prepared from the methods described in WO 2015 / 155075); N'-[5-Bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine (this compound can be prepared from the methods described in IPCOM000249876D); N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenyl-ethyl)phenyl]-N-methyl-formamidine, N'-[4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-methoxy-2-methyl-phenyl]-N-isopropyl-N-methyl-formamidine (these compounds can be prepared from the methods described in WO 2018 / 228896); N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)oxetan-2-yl]phenyl]-N-methyl-formamidine, N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methyl-formamidine (these compounds can be prepared from the methods described in WO 2019 / 110427); N-[(1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide, N-[(1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide, N-[(1R)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide, N-[(1S)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide, 8-fluoro-N-[(1R)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide, 8-fluoro-N-[(1S)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide, N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide, N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide, N-((1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide, N-((1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide (these compounds can be prepared from the methods described in International Publication No. WO 2017 / 153380); 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,6-trifluoro-3,3-dimethyl-isoquinoline, 4,4-difluoro-3,3-dimethyl-1-(6-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline, 4,4-difluoro-3,3-dimethyl-1-(7-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline, 1-(6-chloro-7-methyl-pyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline (these compounds can be prepared from the methods described in International Publication No. WO 2017 / 025510); 1-(4,5-dimethylbenzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline, 1-(4,5-dimethylbenzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline, 6-chloro-4,4-difluoro-3,3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline, 4,4-difluoro-1-(5-fluoro-4-methyl-benzimidazol-1-yl)-3,3-dimethyl-isoquinoline, 3-(4,4-difluoro-3,3-dimethyl-1-isoquinolyl)-7,8-Dihydro-6H-cyclopenta[e]benzimidazole (these compounds can be prepared from the methods described in International Publication No. WO 2016 / 156085), N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylate, N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-1,2,4-triazol-3-amine (these compounds can be prepared from the methods described in International Publication Nos. WO 2017 / 055473, WO 2017 / 055469, WO 2017 / 093348 and WO 2017 / 118689); 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,(4-triazol-1-yl)propan-2-ol (this compound can be prepared from the method described in International Publication No. WO 2017 / 029179); 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol (this compound can be prepared from the method described in International Publication No. WO 2017 / 029179); 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile (this compound can be prepared from the method described in International Publication No. WO 2016 / 156290); 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile (this compound can be prepared from the method described in International Publication No. WO 2016 / 156290); (4-phenoxyphenyl)methyl 2-amino-6-methyl-pyridine-3-carboxylate (this compound can be prepared from the method described in International Publication No. WO 2014 / 006945); 2,6-dimethyl-1H,5H-[1,4]dithieno[2,3-c:5,6-c’]dipyrrole-1,3,5,7(2H,6H)-tetrone (this compound can be prepared from the method described in International Publication No. WO 2011 / 138281) N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide; N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide; (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-penta-3-enamide (this compound can be prepared from the method described in International Publication No. WO 2018 / 153707); N’-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine; N’-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine (this compound can be prepared from the method described in International Publication No. WO 2016 / 202742); 2-(difluoromethyl)-N-[(3S)-3-ethyl-1,1-Dimethyl-inden-4-yl]pyridine-3-carboxamide (this compound can be prepared from the method described in International Publication No. WO2014 / 095675); (5-Methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone, (3-Methylisoxazol-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone (these compounds can be prepared from the method described in International Publication No. WO2017 / 220485); 2-Oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide (this compound can be prepared from the method described in International Publication No. WO2018 / 065414); Ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate (this compound can be prepared from the method described in International Publication No. WO2018 / 158365); 2,2-Difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide, N-[(E)-Methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, N-[(Z)-Methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, N-[N-Methoxy-methyl-carboximidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide (these compounds can be prepared from the method described in International Publication No. WO2018 / 202428); 1-[1-(4-Chlorophenyl)cyclobutyl]ethyl (2S)-2-[(3-Hydroxy-4-methoxy-pyridine-2-carbonyl)-amino]propanoate; [2-(4-Bromo-7-fluoro-indol-1-yl)-1-methyl-propyl](2S)-2-[(3-Hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate; [2-(3,5-dichloro-2-pyridyl)-1-methyl-propyl](2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate; [(1S)-1-[1-(1-naphthyl)cyclopropyl]ethyl](2S)-2-[[3-(acetoxymethoxy)-4-methoxy-pyridine-2-carbonyl]amino]propanoate, [(1S)-1-[1-(1-naphthyl)cyclopropyl]ethyl](2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, [2-[[(1S)-2-[2-(3,5-dichloro-2-pyridyl)-1-methyl-propoxy]-1-methyl-2-oxo-ethyl]carbamoyl]-4-methoxy-3-pyridyl]oxymethyl 2-methylpropanoate, [4-methoxy-2-[[(1S)-1-methyl-2-[(1S)-1-[1-(1-naphthyl)cyclopropyl]ethoxy]-2-oxo-ethyl], Carbamoyl]-3-pyridyl]oxymethyl 2-methylpropanoate; [2-(4-bromophenyl)-1,2-dimethyl-propyl](2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate; 1-(1-phenylcyclohexyl)ethyl(2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate; [1-methyl-2-(2-quinolyl)propyl](2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate; [2-(7-bromoindol-1-yl)-1-methyl-propyl](2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate; [1-methyl-2-[6-(trifluoromethyl)indol-1-yl]propyl](2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, (2-indazol-1-yl-1-methyl-propyl)(2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, [2-(5-chloro-2-thienyl)-1-methyl-propyl](2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, [2-(4,7-dichloroindol-1-yl)-1-methyl-propyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, [2-(7-bromo-4-fluoro-indol-1-yl)-1-methyl-propyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate, [(1S)-1-[1-(1-naphthyl)cyclopropyl]ethyl](2S)-2-[(3-acetoxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate (these compounds can be prepared from the methods described in International Publication No. 2020 / 208096); Methyl N-[[5-[1-(2,6-difluoro-4-isopropyl-phenyl)pyrazol-3-yl]-2-methyl-phenyl]methyl]carbamate;Methyl N-[[5-[1-(4-cyclopropyl-2,6-difluoro-phenyl)pyrazol-3-yl]-2-methyl-phenyl]methyl]carbamate; (2E)-2-methoxyimino-N-methyl-2-[3-methyl-2-[[(E)-1-[4-(trifluoromethyl)-2-pyridyl]ethylideneamino]oxymethyl]phenyl]acetamide; 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide; 6-chloro-N-[2-(2-chloro-4-methyl-phenyl)-2,2-difluoro-ethyl]-3-(3-cyclopropyl-2-fluoro-phenoxy)-5-methyl-pyridazine-4-carboxamide; 6-chloro-3-(3-cyclopropyl-2-fluoro-phenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoro-ethyl]-5-methyl-pyridazine-4-carboxamide; 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)ethyl]pyrimidin-2-amine; 2-(difluoromethyl)-5-[2-[1-(2,6-difluorophenyl)cyclopropoxy]pyrimidin-5-yl]-1,3,4-oxadiazole; 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)cyclopropyl]pyrimidin-2-amine; 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)cyclopropyl]pyrimidin-2-amine; N-[1-(2-fluorophenyl)cyclopropyl]-5-[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]pyrimidin-2-amine; 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)ethyl]pyrimidin-2-amine; 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(3,5-difluorophenyl)ethyl]pyrimidin-2-amine;Ethyl 1-[[4-[[2-(trifluoromethyl)-1,3-dioxolan-2-yl]methoxy]phenyl]methyl]-1H-pyrazole-4-carboxylate; Ethyl 1-[[4-[[(1Z)-2-ethoxy-3,3,3-trifluoro-1-propen-1-yl]oxy]phenyl]methyl]-1H-pyrazole-4-carboxylate; 3-[[3-chloro-2-(2-ethylpyrazol-3-yl)phenyl]methyl]-7,8-difluoro-2-methyl-quinoline; N-[2-(2-ethylpyrazol-3-yl)phenyl]-5,6-difluoro-3-methyl-quinoxalin-2-amine; 5,6-difluoro-N-[3-fluoro-2-(2-propylpyrazol-3-yl)phenyl]-3-methyl-quinoxalin-2-amine; N-[3-chloro-2-(2-propylpyrazol-3-yl)phenyl]-7,8-difluoro-2-methyl-quinolin-3-amine; 1-(5,6-dimethyl-3-pyridyl)-4,4-difluoro-3,3-dimethyl-isoquinoline; 1-[6-(difluoromethyl)-5-methyl-3-pyridyl]-4,4-difluoro-3,3-dimethyl-isoquinoline; Methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoate and 2-(1-chlorocyclopropyl)-1-(2-chlorophenyl)-3-(1,2,4-triazol-1-yl)propan-2-ol.;

[0203] In a preferred embodiment, suitable additional active ingredients are selected from the group consisting of benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, sedaxane, bixafen, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, propiconazole, epoxyconazole, metconazole, tetraconazole, fluoxastrobin, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoate, methyl 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1,2,4-triazol-1-ylmethyl)cyclopentanecarboxylate, flutriafol, mefentrifluconazole, ipconazole, paclobutrazol, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, metalaxyl-M, fenpropimorph, cyprodinil, spiroxamine, mancozeb, chlorothalonil, folpet, copper oxychloride, copper hydroxide, sulfur, oxathiapiprolin, iprovalicarb, quinoxyfen, mandipropamid, fluazinam, fludioxonil, fosetyl-aluminum, acibenzolar-S-methyl, enestrobin, imidacloprid, flupyradifurone, isoflucypram, methyltetraprole, florylpicoxamid, metflupyricoxamid, flufenoxadiazam, isfetamid, procymidone, carbendazim, fenhexamid, prochloraz, prohexadione-calcium, tea tree oil (extract of Melaleuca alternifolia, commercially available as Timorex Gold®, a broad-spectrum biofungicide and biocidal agent derived from plants), N’-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methylformamidine, cyclobutrifluram calcium phosphonate, cis-jasmone, trinexapac-ethyl, glyphosate, 2,4-D (2,4-dichlorophenoxyacetic acid) and thiamethoxam.

[0204] The compounds of the present invention may also be used in combination with anthelmintics. Such anthelmintics include compounds selected from the group of compounds of the macrocyclic lactone class such as ivermectin, abamectin, avermectin, emamectin, eprinomectin, doramectin, selamectin, moxidectin, nemadectin and milbemycin derivatives as described in European Patent No. 357460, European Patent No. 444964 and European Patent No. 594291. Further anthelmintics include semi-synthetic and biosynthetic abamectin / milbemycin derivatives such as those described in US Patent No. 5015630, International Publication No. 9415944 and International Publication No. 9522552. Further anthelmintics include benzimidazoles such as albendazole, cambendazole, fenbendazole, flubendazole, mebendazole, oxfendazole, oxybendazole, parbendazole and other members of this class. Further anthelmintics include imidazothiazoles and tetrahydropyrimidines such as tetramisole, levamisole, pyrantel pamoate, oxantel or morantel. Further anthelmintics include trematocides such as triclabendazole and closantel and cestocides such as praziquantel and epsiprantel.

[0205] The polymorphs of the present invention may also be used in combination with derivatives and analogs of anthelmintics of the paraherquamide / marcfortine class, such as those disclosed in US Patent No. 5478855, US Patent No. 4639771 and German Patent No. 19520936, and anti-parasitic oxazolines.

[0206] The polymorphs of the present invention may be used in combination with derivatives and analogs of the general class of dioxomorpholine antiparasitic agents as described in WO 96 / 15121, and may also be used in combination with anthelmintically effective cyclic depsipeptides such as those described in WO 96 / 11945, WO 93 / 19053, WO 93 / 25543, EP 626375, EP 382173, WO 94 / 19334, EP 382173, and EP 503538.

[0207] The polymorphs of the present invention may be used in combination with other ectoparasiticides; for example, fipronil; pyrethroids; organophosphates; insect growth regulators such as lufenuron; ecdysone agonists such as tebufenozide; and neonicotinoids such as imidacloprid.

[0208] The polymorphs of the present invention may be used in combination with terpene alkaloids such as those described in WO 95 / 19363 or WO 04 / 72086, particularly the compounds disclosed therein.

[0209] Other examples of such biologically active compounds with which the compounds of the present invention may be used in combination include, but are not limited to, the following: Organophosphorus agents: acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, bromophos, bromophos-ethyl, kasugamycin, chlor-ethoxyphos, chlorpyrifos, chlorfenvinphos, chlormephos, demeton, demeton-S-methyl, demeton-S-methyl sulfone, dialifos, diazinon, dichlorvos, dichlorothophos, dimethoate, disulfoton, ethion, etoprophos, ethirimol, famphur, fenamiphos, fenitrothion, fensulfothion, fenthion, flupyrazofos, honohos, formothion, phosphazate, heptenophos, isazofos, isothioate, isoxathion, malathion, methacrifos, methamidophos, methidathion, methyl parathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, paraoxon, parathion, parathion-methyl, phenthoate, hosalon, phosphorane, phosphocarb, phosmet, phosphamidon, phorate, hokxim, pyrimiphos, pyrimiphos-methyl, profenofos, propaphos, proetamphos, prothiofos, pyraclofos, pyridapenthion, quinalphos, sulprofos, temephos, terbufos, tebupirimfos, tetrachlorvinphos, thimet, triazophos, trichlorfon, bamidothion.

[0210] Carbamates: alanycarb, aldicarb, 2-sec-butylphenyl methylcarbamate, benfuracarb, carbaryl, carbofuran, carbosulfan, cloethocarb, ethiofencarb, phenoxycarb, fenthiofencarb, furathiocarb, HCN-801, isoprocarb, indoxacarb, methiocarb, methomyl, 5-methyl-m-cumenyl butyryl (methyl) carbamate, oxamyl, pyrimicarb, propoxur, thiodicarb, thiafenthox, triazamate, UC-51717.

[0211] Pyrethroids: Acrinathrin, Allethrin, Alpha-Methrin, (E)-(1R)-cis-2,2-Dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylic acid 5-benzyl-3-furylmethyl, Bifenthrin, Beta-Cyfluthrin, Cyfluthrin, a-Cypermethrin, Beta-Cypermethrin, Bioallethrin, Bioallethrin ((S)-Cyclopentyl isomer), Bioresthmetrin, Bifenthrin, NCI-85193, Cycloprothrin, Cyhalothrin, Cythithrin, Cyphenothrin, Deltamethrin, Empenthrin, Esfenvalerate, Ethofenprox, Fenfluthrin, Fenpropathrin, Fenvalerate, Flucitrate, Flumethrin, Flubalinate (D isomer), Imiprothrin, Cyhalothrin, Lambda-Cyhalothrin, Permethrin, Phenothrin, Prallethrin, Pyrethrins (natural products), Resmethrin, Tetramethrin, Transfluthrin, Theta-Cypermethrin, Silafluofen, t-Flubalinate, Tefluthrin, Tralomethrin, Zeta-Cypermethrin.

[0212] Arthropod growth regulators: a) Chitin synthesis inhibitors: Benzoyl ureas: Chlorfluazuron, Diflubenzuron, Fluazuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Teflubenzuron, Triflumuron, Buprofezin, Diofenolan, Hexythiazox, Etoxazole, Chlorfentazine; b) Ecdysone antagonists: Halofenozide, Methoxyphenozide, Tebufenozide; c) Juvenoids: Pyriproxyfen, Methoprene (including S-Methoprene), Phenoxycarb; d) Lipid biosynthesis inhibitors: Spirodiclofen.

[0213] Other antiparasitic drugs: Asekinocil, Amitraz, AKD-1022, ANS-118, Azadirachtin, Bacillus thuringiensis, Bensultap, Bifenazate, Binapacryl, Bromopropylate, BTG-504, BTG-505, Camphacryl, Cartap, Chlorobenzilate, Chlordimeform, Chlorfenapyr, Chromafenozide, Clothianidin, Cyromazine, Diafenthiuron, DBI-3204, Dinactin, Dihydroxymethyldihydroxypyrrolidine, Dinobuton, Dinocap, Endosulfan, Ethiprole, Ethofenprox, Fenazaquin, Fluvalinate, MTI-800, Fenpyroximate, Fluacrypyrim, Flubendimine, Flubrocythrinate, Flufenazine, Flufenprox, Fluproxyfen, Halofenprox, Hydramethylnon, IKI-220, Kanemite, NC-196, Neemgard, Nidinorterfuran, Nitenpyram, SD-35651, WL-108477, Pyridalyl, Propargite, Protrifenbute, Pymetrozine, Pyridaben, Pyrimidifen, NC-1111, R-195, RH-0345, RH-2485, RYI-210, S-1283, S-1833, SI-8601, Silfluofen, Cyromazine, Spinosad, Tebufenpyrad, Tetradifon, Tetranactin, Thiacloprid, Thiocyclam, Thiamethoxam, Tolfenpyrad, Triazamate, Triethoxypinosylvin, Trinatactin, Verbutin, Vertalec, YI-5301.

[0214] Biological agents: Bacillus thuringiensis subsp. aizawai, kurstaki, Bacillus thuringiensis delta-endotoxin, Baculovirus, Entomopathogenic bacteria, Viruses and Fungi.

[0215] Bactericides: Chlorotetracycline, Oxytetracycline, Streptomycin.

[0216] Other biological agents: enrofloxacin, febantel, penetramate, meloxicam, cephalexin, kanamycin, pimobendan, clenbuterol, omeprazole, thiamphenicol, benazepril, piriprofen, cefquinome, florfenicol, buserelin, cefovecin, tulathromycin, ceftiour, carprofen, metofluthrin, praziquarantel, triclabendazole.

[0217] The following mixtures of polymorphs and active ingredients are preferred: A compound selected from the group of substances consisting of: petroleum + ((I-A) or (I-B)), 1,1-bis(4-chlorophenyl)-2-ethoxyethanol + ((I-A) or (I-B)), 2,4-dichlorophenylbenzenesulfonate + ((I-A) or (I-B)), 2-fluoro-N-methyl-N-1-cinnamaldehyde + ((I-A) or (I-B)), 4-chlorophenylphenylsulfone + ((I-A) or (I-B)), acetoprole + ((I-A) or (I-B)), aldoxycarb + ((I-A) or (I-B)), amidithion + ((I-A) or (I-B)), amido thioate + ((I-A) or (I-B)), amiton + ((I-A) or (I-B)), hydrogen oxalate amiton + ((I-A) or (I-B)), amitraz + ((I-A) or (I-B)), aramite + ((I-A) or (I-B)), arsenic trioxide + ((I-A) or (I-B)), azobenzene + ((I-A) or (I-B)), azothoate + ((I-A) or (I-B)), benomyl + ((I-A) or (I-B)), benoxaphos + ((I-A) or (I-B)), benzyl benzoate + ((I-A) or (I-B)), bixafen + ((I-A) or (I-B)), brofenvalerate + ((I-A) or (I-B)), bromocyclene + ((I-A) or (I-B)), bromophos + ((I-A) or (I-B)), bromopropylate + ((I-A) or (I-B)), buprofezin + ((I-A) or (I-B)), butocarboxim + ((I-A) or (I-B)), butoxycarboxim + ((I-A) or (I-B)), butylpyridaben + ((I-A) or (I-B)), calcium polysulfide + ((I-A) or (I-B)), camphechlor + ((I-A) or (I-B)), carbaryl + ((I-A) or (I-B)), carbophenothion + ((I-A) or (I-B)), cymiazole + ((I-A) or (I-B)), chinomethionat + ((I-A) or (I-B)), chlorbenside + ((I-A) or (I-B)), chlordimeform + ((I-A) or (I-B)), chlordimeform hydrochloride + ((I-A) or (I-B)), chlorphenethol + ((I-A) or (I-B)), chlorfenson + ((I-A) or (I-B)),Chlorophensulfide + ((I-A) or (I-B)), Chlorobenzilate + ((I-A) or (I-B)), Chloromethiuron + ((I-A) or (I-B)), Chloropropylate + ((I-A) or (I-B)), Chlorothiophos + ((I-A) or (I-B)), Cineole I + ((I-A) or (I-B)), Cineole II + ((I-A) or (I-B)), Cineole S + ((I-A) or (I-B)), Chrysanthemum + ((I-A) or (I-B)), Coumaphos + ((I-A) or (I-B)), Chlorotrimeton + ((I-A) or (I-B)), Crotoxyphos + ((I-A) or (I-B)), Cufraeb + ((I-A) or (I-B)), Cyanthoate + ((I-A) or (I-B)), DCPM + ((I-A) or (I-B)), DDT + ((I-A) or (I-B)), Demephion + ((I-A) or (I-B)), Demephion-O + ((I-A) or (I-B)), Demephion-S + ((I-A) or (I-B)), Demeton-methyl + ((I-A) or (I-B)), Demeton-O + ((I-A) or (I-B)), Demeton-O-methyl + ((I-A) or (I-B)), Demeton-S + ((I-A) or (I-B)), Demeton-S-methyl + ((I-A) or (I-B)), Demeton-S-methylsulfone + ((I-A) or (I-B)), Dichlofluanid + ((I-A) or (I-B)), Dichlorvos + ((I-A) or (I-B)), Dicriphos + ((I-A) or (I-B)), Dienochlor + ((I-A) or (I-B)), Dimethoate + ((I-A) or (I-B)), Dinex + ((I-A) or (I-B)), Dinex Dicrexine + ((I-A) or (I-B)), Dinocap-4 + ((I-A) or (I-B)), Dinocap-6 + ((I-A) or (I-B)), Dinoceton + ((I-A) or (I-B)), Dinopenton + ((I-A) or (I-B)), Dinosulfone + ((I-A) or (I-B)), Dinoterbon + ((I-A) or (I-B)), Dioxathion + ((I-A) or (I-B)), Diphenylsulfone + ((I-A) or (I-B)), Disulfiram + ((I-A) or (I-B)), DNOC + ((I-A) or (I-B)),Dofenapine + ((I-A) or (I-B)), Dramectin + ((I-A) or (I-B)), Endothion + ((I-A) or (I-B)), Eprinomectin + ((I-A) or (I-B)), Ethoate methyl + ((I-A) or (I-B)), Ethirimfos + ((I-A) or (I-B)), Phenazafur + ((I-A) or (I-B)), Fenbutatin oxide + ((I-A) or (I-B)), Phenothiocarb + ((I-A) or (I-B)), Fenpyram + ((I-A) or (I-B)), Fenpyroximate + ((I-A) or (I-B)), Fenpyrazamine + ((I-A) or (I-B)), Fenson + ((I-A) or (I-B)), Fentrifanil + ((I-A) or (I-B)), Flubendiamide + ((I-A) or (I-B)), Flucycloxuron + ((I-A) or (I-B)), Fluenechil + ((I-A) or (I-B)), Fluorobenzide + ((I-A) or (I-B)), FMC1137 + ((I-A) or (I-B)), Formetanate + ((I-A) or (I-B)), Formetanate hydrochloride + ((I-A) or (I-B)), Formparanate + ((I-A) or (I-B)), γ-HCH + ((I-A) or (I-B)), Gliotoxin + ((I-A) or (I-B)), Halfenprox + ((I-A) or (I-B)), Hexadecyl cyclopropanecarboxylate + ((I-A) or (I-B)), Isocarbophos + ((I-A) or (I-B)), Jasmonin I + ((I-A) or (I-B)), Jasmonin II + ((I-A) or (I-B)), Iodofenphos + ((I-A) or (I-B)), Lindane + ((I-A) or (I-B)), Malonoben + ((I-A) or (I-B)), Mecarbam + ((I-A) or (I-B)), Methoprophos + ((I-A) or (I-B)), Mesulfen + ((I-A) or (I-B)), Methacrifos + ((I-A) or (I-B)), Methyl bromide + ((I-A) or (I-B)), Methiocarb + ((I-A) or (I-B)), Mexacarbate + ((I-A) or (I-B)), Milbemycin oxime + ((I-A) or (I-B)), Mipafox + ((I-A) or (I-B)), Monocrotophos + ((I-A) or (I-B)), Morphothion + ((I-A) or (I-B)), Moxidectin + ((I-A) or (I-B)), Naled + ((I-A) or (I-B)), 4-Chloro-2-(2-chloro-2-methyl-propyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazin-3-one + ((I-A) or (I-B)), Nifluridide + ((I-A) or (I-B)), Nikkomycin + ((I-A) or (I-B)), Nitrilacarb + ((I-A) or (I-B)), Nitrilacarb 1:1 zinc chloride complex + ((I-A) or (I-B)), Omethoate + ((I-A) or (I-B)), Oxydeprofos + ((I-A) or (I-B)), Oxydisulfoton + ((I-A) or (I-B)), pp’-DDT + ((I-A) or (I-B)), Parathion + ((I-A) or (I-B)), Permethrin + ((I-A) or (I-B)), Fencapton + ((I-A) or (I-B)), Phosalone + ((I-A) or (I-B)), Phospholane + ((I-A) or (I-B)), Phosphamidon + ((I-A) or (I-B)), Polychlorotepene + ((I-A) or (I-B)), Polyactin + ((I-A) or (I-B)), Proclonol + ((I-A) or (I-B)), Promacyl + ((I-A) or (I-B)), Propoxur + ((I-A) or (I-B)), Prothidathion + ((I-A) or (I-B)), Prothoate + ((I-A) or (I-B)), Pyrethrin I + ((I-A) or (I-B)), Pyrethrin II + ((I-A) or (I-B)), Pyrethrin + ((I-A) or (I-B)), Pyridaphenthion + ((I-A) or (I-B)), Pyrimitate + ((I-A) or (I-B)), Quinalphos + ((I-A) or (I-B)), Quincholphos + ((I-A) or (I-B)), R-1492 + ((I-A) or (I-B)), Phosphoglycine + ((I-A) or (I-B)), Rotenone + ((I-A) or (I-B)), Schradan + ((I-A) or (I-B)), Cephusphos + ((I-A) or (I-B)), Selamectin + ((I-A) or (I-B)), Sofamide + ((I-A) or (I-B)), SSI-121 + ((I-A) or (I-B)), Sulfiram + ((I-A) or (I-B)), Sulfuryl fluoride + ((I-A) or (I-B))Sulphotep + ((I-A) or (I-B)), sulfur + ((I-A) or (I-B)), diflubenzuron + ((I-A) or (I-B)), τ-fluorovalinate + ((I-A) or (I-B)), TEPP + ((I-A) or (I-B)), terbum + ((I-A) or (I-B)), tetradifon + ((I-A) or (I-B)), tetrasul + ((I-A) or (I-B)), thiophenox + ((I-A) or (I-B)), thiocarb + ((I-A) or (I-B)), thiofanox + ((I-A) or (I-B)), thiometon + ((I-A) or (I-B)), thioquinox + ((I-A) or (I-B)), turpentinel + ((I-A) or (I-B)), triamiphos + ((I-A) or (I-B)), triarathene + ((I-A) or (I-B)), triazophos + ((I-A) or (I-B)), triazuron + ((I-A) or (I-B)), triphenophos + ((I-A) or (I-B)), trinactin + ((I-A) or (I-B)), bamidothion + ((I-A) or (I-B)), vaniliprole + ((I-A) or (I-B)), vetoxazine + ((I-A) or (I-B)), copper octanoate + ((I-A) or (I-B)), copper sulfate + ((I-A) or (I-B)), sibuthrin + ((I-A) or (I-B)), dicloran + ((I-A) or (I-B)), dichlorophen + ((I-A) or (I-B)), endothal + ((I-A) or (I-B)), fentin + ((I-A) or (I-B)), slaked lime + ((I-A) or (I-B)), nerverm + ((I-A) or (I-B)), quinoclamine + ((I-A) or (I-B)), quinoneamide + ((I-A) or (I-B)), simazine + ((I-A) or (I-B)), triphenyltin acetate + ((I-A) or (I-B)), triphenyltin hydroxide + ((I-A) or (I-B)), crophomate + ((I-A) or (I-B)), piperazine + ((I-A) or (I-B)), thiophanate + ((I-A) or (I-B)), chloralose + ((I-A) or (I-B)), fenitrothion + ((I-A) or (I-B)), pyridin-4-amine + ((I-A) or (I-B)), strychnine + ((I-A) or (I-B))1-Hydroxy-1H-pyridine-2-thione + ((I-A) or (I-B)), 4-(quinoxalin-2-ylamino)benzenesulfonamide + ((I-A) or (I-B)), 8-hydroxyquinoline sulfate + ((I-A) or (I-B)), bronopol + ((I-A) or (I-B)), copper hydroxide + ((I-A) or (I-B)), cresol + ((I-A) or (I-B)), dipyrithione + ((I-A) or (I-B)), dodine + ((I-A) or (I-B)), fenaminosulf + ((I-A) or (I-B)), formaldehyde + ((I-A) or (I-B)), hydralgafen + ((I-A) or (I-B)), kasugamycin + ((I-A) or (I-B)), kasugamycin hydrochloride hydrate + ((I-A) or (I-B)), nickel bis(dimethyldithiocarbamate) + ((I-A) or (I-B)), nitrapyrin + ((I-A) or (I-B)), octhilinone + ((I-A) or (I-B)), oxolinic acid + ((I-A) or (I-B)), oxytetracycline + ((I-A) or (I-B)), potassium hydroxyquinoline sulfate + ((I-A) or (I-B)), probenazole + ((I-A) or (I-B)), streptomycin + ((I-A) or (I-B)), streptomycin sesquisulfate + ((I-A) or (I-B)), tecnazene + ((I-A) or (I-B)), thimerosal + ((I-A) or (I-B)), Adoxophyes orana GV + ((I-A) or (I-B)), Agrobacterium radiobacter + ((I-A) or (I-B)), Amblyseius spp. + ((I-A) or (I-B)), Anagrapha falcifera NPV + ((I-A) or (I-B)), Anagrus atomus + ((I-A) or (I-B)), Aphelinus abdominalis + ((I-A) or (I-B)), Aphidius colemani + ((I-A) or (I-B)),Aphidoletes aphidimyza + ((I-A) or (I-B)), Autographa californica NPV + ((I-A) or (I-B)), Bacillus sphaericus Neide + ((I-A) or (I-B)), Beauveria brongniartii + ((I-A) or (I-B)), Chrysoperla carnea + ((I-A) or (I-B)), Cryptolaemus montrouzieri + ((I-A) or (I-B)), Cydia pomonella GV + ((I-A) or (I-B)), Dacnusa sibirica + ((I-A) or (I-B)), Diglyphus isaea + ((I-A) or (I-B)), Encarsia formosa + ((I-A) or (I-B)), Eretmocerus eremicus + ((I-A) or (I-B)), Heterorhabditis bacteriophora and H. megidis + ((I-A) or (I-B)), Hippodamia convergens + ((I-A) or (I-B)), Leptomastix dactylopii + ((I-A) or (I-B)), Macrolophus caliginosus + ((I-A) or (I-B)), Mamestra brassicae NPV + ((I-A) or (I-B)), Metaphycus helvolus + ((I-A) or (I-B)), Metarhizium anisopliae var. acridum + ((I-A) or (I-B)),Metarhizium anisopliae var. anisopliae + ((I-A) or (I-B)), Neodiprion sertifer NPV and N. lecontei NPV + ((I-A) or (I-B)), Orius spp. + ((I-A) or (I-B)), Paecilomyces fumosoroseus + ((I-A) or (I-B)), Phytoseiulus persimilis + ((I-A) or (I-B)), Steinernema bibionis + ((I-A) or (I-B)) Steinernema carpocapsae + ((I - A) or (I - B)), Steinernema feltiae + ((I - A) or (I - B)), Steinernema glaseri + ((I - A) or (I - B)), Steinernema riobrave b + ((I - A) or (I - B)), Steinernema riobravis + ((I - A) or (I - B)), Steinernema scapterisci + ((I - A) or (I - B)), Steinernema spp. + ((I - A) or (I - B)), Trichogramma spp. + ((I - A) or (I - B)), Typhlodromus occidentalis + ((I - A) or (I - B)), Verticillium lecanii + ((I - A) or (I - B)), aldicarb + ((I - A) or (I - B)), bixazil + ((I - A) or (I - B)), busulfan + ((I - A) or (I - B)), dimethipin + ((I - A) or (I - B)), hemer + ((I - A) or (I - B)), hempa + ((I - A) or (I - B)), metepa + ((I - A) or (I - B)), methiotepa + ((I - A) or (I - B)), methyl aldicarb + ((I - A) or (I - B)), molinate + ((I - A) or (I - B)), penfluron + ((I - A) or (I - B)), tepa + ((I - A) or (I - B)), thiohempa + ((I - A) or (I - B)), thiotepa + ((I - A) or (I - B)), tretamine + ((I - A) or (I - B)), uredepa + ((I - A) or (I - B)), (E)-deca-5-en-1-yl acetate + (E)-deca-5-en-1-ol + ((I - A) or (I - B)), (E)-trideca-4-en-1-yl acetate + ((I - A) or (I - B)), (E)-6-methylhepta-2-en-4-ol + ((I - A) or (I - B)),(E,Z)-tetradeca-4,10-dien-1-yl acetate + ((I-A) or (I-B)), (Z)-dodeca-7-en-1-yl acetate + ((I-A) or (I-B)), (Z)-hexadeca-11-enal + ((I-A) or (I-B)), (Z)-hexadeca-11-en-1-yl acetate + ((I-A) or (I-B)), (Z)-hexadeca-13-en-11-yn-1-yl acetate + ((I-A) or (I-B)), (Z)-icos-13-en-10-one + ((I-A) or (I-B)), (Z)-tetradeca-7-en-1-al + ((I-A) or (I-B)), (Z)-tetradeca-9-en-1-ol + ((I-A) or (I-B)), (Z)-tetradeca-9-en-1-yl acetate + ((I-A) or (I-B)), (7E,9Z)-dodeca-7,9-dien-1-yl acetate + ((I-A) or (I-B)), (9Z,11E)-tetradeca-9,11-dien-1-yl acetate + ((I-A) or (I-B)), (9Z,12E)-tetradeca-9,12-dien-1-yl acetate + ((I-A) or (I-B)), 14-methyloctadec-1-ene + ((I-A) or (I-B)), 4-methylnonan-5-ol + 4-methylnonan-5-one + ((I-A) or (I-B)), α-multistriatin + ((I-A) or (I-B)), brevicomin + ((I-A) or (I-B)), codlelure + ((I-A) or (I-B)), codlemone + ((I-A) or (I-B)), querelure + ((I-A) or (I-B)), disparlure + ((I-A) or (I-B)), dodeca-8-en-1-yl acetate + ((I-A) or (I-B)), dodeca-9-en-1-yl acetate + ((I-A) or (I-B)), dodeca-8,10-dien-1-yl acetate + ((I-A) or (I-B)), dominicalure + ((I-A) or (I-B)), ethyl 4-methyloctanoate + ((I-A) or (I-B)), eugenol + ((I-A) or (I-B)), frontalin + ((I-A) or (I-B)), grandlure + ((I-A) or (I-B)), grandlure I + ((I-A) or (I-B)), grandlure II + ((I-A) or (I-B))Grandlure III + ((I-A) or (I-B)), Grandlure IV + ((I-A) or (I-B)), Hexalure + ((I-A) or (I-B)), Ipsdienol + ((I-A) or (I-B)), Ipsenol + ((I-A) or (I-B)), Japonilure + ((I-A) or (I-B)), Linalool + ((I-A) or (I-B)), Litlure + ((I-A) or (I-B)), Looplure + ((I-A) or (I-B)), Medlure + ((I-A) or (I-B)), Megatomonic acid + ((I-A) or (I-B)), Methyl eugenol + ((I-A) or (I-B)), Muscalure + ((I-A) or (I-B)), Octadeca-2,13-dien-1-yl acetate + ((I-A) or (I-B)), Octadeca-3,13-dien-1-yl acetate + ((I-A) or (I-B)), Orflure + ((I-A) or (I-B)), Orictalure + ((I-A) or (I-B)), Ostramone + ((I-A) or (I-B)), Siglure + ((I-A) or (I-B)), Soldiagem + ((I-A) or (I-B)), Sulcatol + ((I-A) or (I-B)), Tetradeca-11-en-1-yl acetate + ((I-A) or (I-B)), Trimedlure + ((I-A) or (I-B)), Trimedlure A + ((I-A) or (I-B)), Trimedlure B1 + ((I-A) or (I-B)), Trimedlure B2 + ((I-A) or (I-B)), Trimedlure C + ((I-A) or (I-B)), Trunc-call + ((I-A) or (I-B)), 2-(Octylthio)ethanol + ((I-A) or (I-B)), Butapironoxyl + ((I-A) or (I-B)), Butoxy(polypropylene glycol) + ((I-A) or (I-B)), Dibutyl adipate + ((I-A) or (I-B)), Dibutyl phthalate + ((I-A) or (I-B)), Dibutyl succinate + ((I-A) or (I-B)), Diethyltoluamide + ((I-A) or (I-B)), Dimethyl carbonate + ((I-A) or (I-B)), Dimethyl phthalate + ((I-A) or (I-B)), Ethylhexanediol + ((I-A) or (I-B)), Hexamide + ((I-A) or (I-B)), Methokin-butyl + ((I-A) or (I-B)),Methyl neodecanamide + ((I-A) or (I-B)), Oxamate + ((I-A) or (I-B)), Picaridin + ((I-A) or (I-B)), 1,1-Dichloro-1-nitroethane + ((I-A) or (I-B)), 1,1-Dichloro-2,2-bis(4-ethylphenyl)ethane + ((I-A) or (I-B)), 1,2-Dichloropropane + 1,3-Dichloropropene + ((I-A) or (I-B)), 1-Bromo-2-chloroethane + ((I-A) or (I-B)), Ethyl 2,2,2-trichloro-1-(3,4-dichlorophenyl)acetate + ((I-A) or (I-B)), 2,2-Dichlorovinyl 2-ethylsulfinylethyl methyl phosphate + ((I-A) or (I-B)), 2-(1,3-Dithiolan-2-yl)phenyl dimethylcarbamate + ((I-A) or (I-B)), 2-(2-Butoxyethoxy)ethyl thiocyanate + ((I-A) or (I-B)), 2-(4,5-Dimethyl-1,3-dioxolan-2-yl)phenyl methylcarbamate + ((I-A) or (I-B)), 2-(4-Chloro-3,5-xylyloxy)ethanol + ((I-A) or (I-B)), 2-Chlorovinyl diethyl phosphate + ((I-A) or (I-B)), 2-Imidazolidone + ((I-A) or (I-B)), 2-Isovalerylindane-1,3-dione + ((I-A) or (I-B)), 2-Methyl(prop-2-ynyl)aminophenyl methylcarbamate + ((I-A) or (I-B)), 2-Thiocyanatoethyl laurate + ((I-A) or (I-B)), 3-Bromo-1-chloroprop-1-ene + ((I-A) or (I-B)), 3-Methyl-1-phenylpyrazol-5-yl dimethylcarbamate + ((I-A) or (I-B)), 4-Methyl(prop-2-ynyl)amino-3,5-xylyl methylcarbamate + ((I-A) or (I-B)), 5,5-Dimethyl-3-oxocyclohex-1-enyl dimethylcarbamate + ((I-A) or (I-B)), Acetione + ((I-A) or (I-B)), Acrylonitrile + ((I-A) or (I-B)), Aldrin + ((I-A) or (I-B)), Allosamidin + ((I-A) or (I-B)), Alicyclab + ((I-A) or (I-B)), α-Ecdysone + ((I-A) or (I-B)),Aluminum phosphide + ((I-A) or (I-B)), aminocarb + ((I-A) or (I-B)), anabasine + ((I-A) or (I-B)), acetithion + ((I-A) or (I-B)), azamethiphos + ((I-A) or (I-B)), Bacillus thuringiensis δ-endotoxin + ((I-A) or (I-B)), barium hexafluorosilicate + ((I-A) or (I-B)), barium polysulfide + ((I-A) or (I-B)), barthrin + ((I-A) or (I-B)), Bayer 22 / 190 + ((I-A) or (I-B)), Bayer 22408 + ((I-A) or (I-B)), β-cyfluthrin + ((I-A) or (I-B)), β-cyphenothrin + ((I-A) or (I-B)), bioethanomethrin + ((I-A) or (I-B)), biopermethrin + ((I-A) or (I-B)), bis(2-chloroethyl) ether + ((I-A) or (I-B)), sodium borate + ((I-A) or (I-B)), bromfenvinfos + ((I-A) or (I-B)), bromo-DDT + ((I-A) or (I-B)), bufencarb + ((I-A) or (I-B)), butacarb + ((I-A) or (I-B)), butathiofos + ((I-A) or (I-B)), butonate + ((I-A) or (I-B)), calcium arsenate + ((I-A) or (I-B)), calcium cyanide + ((I-A) or (I-B)), carbon disulfide + ((I-A) or (I-B)), carbon tetrachloride + ((I-A) or (I-B)), cartap hydrochloride + ((I-A) or (I-B)), sebacine + ((I-A) or (I-B)), chlorbicyclen + ((I-A) or (I-B)), chlordane + ((I-A) or (I-B)), chlordecone + ((I-A) or (I-B)), chloroform + ((I-A) or (I-B)), chloropicrin + ((I-A) or (I-B)), chloroxime + ((I-A) or (I-B)), chlorprophos + ((I-A) or (I-B)), cis-resmethrin + ((I-A) or (I-B)), cismethrin + ((I-A) or (I-B)), chlorthrin + ((I-A) or (I-B)), copper acetoarsenite + ((I-A) or (I-B)),Copper arsenite + ((I-A) or (I-B)), copper oleate + ((I-A) or (I-B)), cumitoate + ((I-A) or (I-B)), cryolite + ((I-A) or (I-B)), CS708 + ((I-A) or (I-B)), cyanofenphos + ((I-A) or (I-B)), cyanophos + ((I-A) or (I-B)), cyclotrin + ((I-A) or (I-B)), sitioate + ((I, -A) or (I-B)), d-tetramethrin + ((I-A) or (I-B)), DAEP + ((I-A) or (I-B)), dazomet + ((I-A) or (I-B)), decarbofuran + ((I-A) or (I-B)), diazinon + ((I-A) or (I-B)), dicapthon + ((I-A) or (I-B)), dichlorvos + ((I-A) or (I-B)), dicresyl + ((I-A) or (I-B)), dicyclanil + ((I-A) or (I-B)), dieldrin + ((I-A) or (I-B)), diethyl 5-methylpyrazol-3-yl phosphate + ((I-A) or (I-B)), dicrotophos + ((I-A) or (I-B)), dimefluthrin + ((I-A) or (I-B)), dimethoate + ((I-A) or (I-B)), dimethrin + ((I-A) or (I-B)), dimethylvinphos + ((I-A) or (I-B)), dimethirimol + ((I-A) or (I-B)), dinocap + ((I-A) or (I-B)), dinosam + ((I-A) or (I-B)), dinoseb + ((I-A) or (I-B)), dioxabenzofos + ((I-A) or (I-B)), dithicrofos + ((I-A) or (I-B)), DSP + ((I-A) or (I-B)), ecdysterone + ((I-A) or (I-B)), EI 1642 + ((I-A) or (I-B)), EMPC + ((I-A) or (I-B)), EPBP + ((I-A) or (I-B)), ethion + ((I-A) or (I-B)), ethiofencarb + ((I-A) or (I-B)), ethyl formate + ((I-A) or (I-B)), ethylene dibromide + ((I-A) or (I-B)), dichloroethane + ((I-A) or (I-B)), ethylene oxide + ((I-A) or (I-B)), EXD + ((I-A) or (I-B)), fenchlorphos + ((I-A) or (I-B)), fenethacarb + ((I-A) or (I-B)), fenitrothion + ((I-A) or (I-B)), fenoxacrim + ((I-A) or (I-B)), fenpyroximate + ((I-A) or (I-B)), fenthion-ethyl + ((I-A) or (I-B)), flucofuron + ((I-A) or (I-B)),Hosmet + ((I-A) or (I-B)), fosethyl-Al + ((I-A) or (I-B)), fosthietan + ((I-A) or (I-B)), flutolanil + ((I-A) or (I-B)), furethrin + ((I-A) or (I-B)), guazatine + ((I-A) or (I-B)), guazatine acetate + ((I-A) or (I-B)), sodium tetrathiocarboxylate + ((I-A) or (I-B)), halfenprox + ((I-A) or (I-B)), HCH + ((I-A) or (I-B)), HEOD + ((I-A) or (I-B)), heptachlor + ((I-A) or (I-B)), heterophos + ((I-A) or (I-B)), HHDN + ((I-A) or (I-B)), hydrogen cyanide + ((I-A) or (I-B)), hikutin + ((I-A) or (I-B)), IPSP + ((I-A) or (I-B)), isazophos + ((I-A) or (I-B)), isobenzan + ((I-A) or (I-B)), isodrin + ((I-A) or (I-B)), isofenphos + ((I-A) or (I-B)), isolan + ((I-A) or (I-B)), isoprothiolane + ((I-A) or (I-B)), isoxathion + ((I-A) or (I-B)), juvenile hormone I + ((I-A) or (I-B)), juvenile hormone II + ((I-A) or (I-B)), juvenile hormone III + ((I-A) or (I-B)), kelthane + ((I-A) or (I-B)), kinoprene + ((I-A) or (I-B)), lead arsenate + ((I-A) or (I-B)), leptophos + ((I-A) or (I-B)), lirimfos + ((I-A) or (I-B)), lithidathion + ((I-A) or (I-B)), m-cumenyl methylcarbamate + ((I-A) or (I-B)), magnesium phosphide + ((I-A) or (I-B)), magidox + ((I-A) or (I-B)), mecarbam + ((I-A) or (I-B)), menazon + ((I-A) or (I-B)), mercurous chloride + ((I-A) or (I-B)), mesulfenphos + ((I-A) or (I-B)), metam + ((I-A) or (I-B)), metam-potassium + ((I-A) or (I-B)), metam-sodium + ((I-A) or (I-B)), methane sulfonyl fluoride + ((I-A) or (I-B))Metoclothos + ((I-A) or (I-B)), Methoprene + ((I-A) or (I-B)), Metothrin + ((I-A) or (I-B)), Methoxychlor + ((I-A) or (I-B)), Methyl isothiocyanate + ((I-A) or (I-B)), Methyl chloroform + ((I-A) or (I-B)), Methylene chloride + ((I-A) or (I-B)), Methoxadiazone + ((I-A) or (I-B)), Mirex + ((I-A) or (I-B)), Naphthalophos + ((I-A) or (I-B)), Naphthalene + ((I-A) or (I-B)), NC-170 + ((I-A) or (I-B)), Nicotine + ((I-A) or (I-B)), Nicotine sulfate + ((I-A) or (I-B)), Nithiazine + ((I-A) or (I-B)), Nor nicotine + ((I-A) or (I-B)), O-5-dichloro-4-iodophenyl O-ethyl ethylphosphonothioate + ((I-A) or (I-B)), O,O-diethyl O-4-methyl-2-oxo-2H-chromen-7-yl phosphorothionate + ((I-A) or (I-B)), O,O-diethyl O-6-methyl-2-propylpyrimidin-4-yl phosphorothionate + ((I-A) or (I-B)), O,O,O’,O’-tetrapropyl dithiopyrophosphate + ((I-A) or (I-B)), Oleic acid + ((I-A) or (I-B)), Para-dichlorobenzene + ((I-A) or (I-B)), Parathion-methyl + ((I-A) or (I-B)), Pentachlorophenol + ((I-A) or (I-B)), Pentachlorophenyl laurate + ((I-A) or (I-B)), PH60-38 + ((I-A) or (I-B)), Pencapton + ((I-A) or (I-B)), Phosphonitril chloride + ((I-A) or (I-B)), Phosphine + ((I-A) or (I-B)), Hokxim-methyl + ((I-A) or (I-B)), Pirimiphos + ((I-A) or (I-B)), Polychlorodicyclopentadiene isomers + ((I-A) or (I-B)), Potassium arsenite + ((I-A) or (I-B)), Potassium thiocyanate + ((I-A) or (I-B)), Precocene I + ((I-A) or (I-B)), Precocene II + ((I-A) or (I-B)), Precocene III + ((I-A) or (I-B))Pirimiphos + ((I - A) or (I - B)), Profenofos + ((I - A) or (I - B)), Promecarb + ((I - A) or (I - B)), Prothiofos + ((I - A) or (I - B)), Pyrazophos + ((I - A) or (I - B)), Pyrethrins + ((I - A) or (I - B)), Cythioate + ((I - A) or (I - B)), Quinalphos - methyl + ((I - A) or (I - B)), Quinothion + ((I - A) or (I - B)), Rafoxanide + ((I - A) or (I - B)), Resmethrin + ((I - A) or (I - B)), Rotenone + ((I - A) or (I - B)), Cadetrin + ((I - A) or (I - B)), Ryania + ((I - A) or (I - B)), Ryanodine + ((I - A) or (I - B)), Sabadilla + ((I - A) or (I - B)), Schradan + ((I - A) or (I - B)), Cephus + ((I - A) or (I - B)), SI - 0009 + ((I - A) or (I - B)), Thiabronil + ((I - A) or (I - B)), Sodium arsenite + ((I - A) or (I - B)), Sodium cyanide + ((I - A) or (I - B)), Sodium fluoride + ((I - A) or (I - B)), Sodium hexafluorosilicate + ((I - A) or (I - B)), Sodium pentachlorophenoxide + ((I - A) or (I - B)), Sodium selenate + ((I - A) or (I - B)), Sodium thiocyanate + ((I - A) or (I - B)), Spinosad + ((I - A) or (I - B)), Spinosad - sodium + ((I - A) or (I - B)), Sulfuryl fluoride + ((I - A) or (I - B)), Suprofol + ((I - A) or (I - B)), Tall oil + ((I - A) or (I - B)), Thionazin + ((I - A) or (I - B)), TDE + ((I - A) or (I - B)), Tebupirimiphos + ((I - A) or (I - B)), Temephos + ((I - A) or (I - B)), Teralethrin + ((I - A) or (I - B)), Tetrachloroethane + ((I - A) or (I - B)), Chlorpyrifos + ((I - A) or (I - B)), Thiosyclam + ((I - A) or (I - B)), Thiosyclam hydrogen oxalate + ((I - A) or (I - B)), Thionazin + ((I - A) or (I - B)), Thiosultap + ((I - A) or (I - B)),Thiosultap-sodium + ((I-A) or (I-B)), Tralometrin + ((I-A) or (I-B)), Transpermethrin + ((I-A) or (I-B)), Triazamate + ((I-A) or (I-B)), Trichlorometaphos-3 + ((I-A) or (I-B)), Trichloronate + ((I-A) or (I-B)), Trimethacarb + ((I-A) or (I-B)), Tolprocarb + ((I-A) or (I-B)), Trichlorpyrifos-methyl + ((I-A) or (I-B)), Triprene + ((I-A) or (I-B)), Veratridine + ((I-A) or (I-B)), Veratrin + ((I-A) or (I-B)), XMC + ((I-A) or (I-B)), Zeta-cypermethrin + ((I-A) or (I-B)), Zinc phosphide + ((I-A) or (I-B)), Zolaprofos + ((I-A) or (I-B)), and Mepralfluthrin + ((I-A) or (I-B)), Tetramethylfluthrin + ((I-A) or (I-B)), Bis(tributyltin) oxide + ((I-A) or (I-B)), Bromoacetamide + ((I-A) or (I-B)), Ferric phosphate + ((I-A) or (I-B)), Niclosamide-olamine + ((I-A) or (I-B)), Tributyltin oxide + ((I-A) or (I-B)), Pyrimorph + ((I-A) or (I-B)), Trifenmorph + ((I-A) or (I-B)), 1,2-Dibromo-3-chloropropane + ((I-A) or (I-B)), 1,3-Dichloropropene + ((I-A) or (I-B)), 3,4-Dichlorotetrahydrothiophene 1,1-dioxide + ((I-A) or (I-B)), 3-(4-Chlorophenyl)-5-methylrhodanine + ((I-A) or (I-B)), 5-Methyl-6-thioxo-1,3,5-thiadiazinan-3-ylacetic acid + ((I-A) or (I-B)), 6-Isopentenylaminopurine + ((I-A) or (I-B)), Anisifloropurine + ((I-A) or (I-B)), Benclothiaz + ((I-A) or (I-B)), Cytokinin + ((I-A) or (I-B)), DCIP + ((I-A) or (I-B)), Lufenuron + ((I-A) or (I-B)), Isamidofos + ((I-A) or (I-B)), Kinetin + ((I-A) or (I-B)),Myrothecium verrucaria composition + ((I-A) or (I-B)), tetrachlorothiophene + ((I-A) or (I-B)), xylenols + ((I-A) or (I-B)), zeatin + ((I-A) or (I-B)), potassium ethylxanthate + ((I-A) or (I-B)), acibenzolar + ((I-A) or (I-B)), acibenzolar-S-methyl, +((I-A) or (I-B)), Japanese knotweed (Reynoutria sachalinensis) extract +((I-A) or (I-B)), α-chlorohydrin +((I-A) or (I-B)), ants +((I-A) or (I-B)), barium carbonate +((I-A) or (I-B)), bisthiosemi +((I-A) or (I-B)), brodifacoum +((I-A) or (I-B)), bromadiolone +((I-A) or (I-B)), bromethalin +((I-A) or (I-B)), chlorophacinone +((I-A) or (I-B)), cholecalciferol +((I-A) or (I-B)), cumachlor +((I-A) or (I-B)), cumafuril +((I-A) or (I-B)), cumatetralyl +((I-A) or (I-B)), crimidine +((I-A) or (I-B)), diphenacoum +((I-A) or (I-B)), diphacinone +((I-A) or (I-B)), difethialone +((I-A) or (I-B)), ergocalciferol +((I-A) or (I-B)), flocoumafen +((I-A) or (I-B)), fluoroacetamide +((I-A) or (I-B)), flupropazate +((I-A) or (I-B)), flupropazate hydrochloride +((I-A) or (I-B)), norbormide +((I-A) or (I-B)), phosphoacetim +((I-A) or (I-B)), phosphorus +((I-A) or (I-B)), pindone +((I-A) or (I-B)), pyrinuron +((I-A) or (I-B)), silymarin +((I-A) or (I-B)), sodium fluoroacetate +((I-A) or (I-B)), potassium sulfate +((I-A) or (I-B)), warfarin +((I-A) or (I-B)), 2-(2-butoxyethoxy)ethyl piperonyl ether +((I-A) or (I-B)), 5-(1,3-benzodioxol-5-yl)-3-hexylcyclohex-2-enone +((I-A) or (I-B)), farnesol + nerolidol +((I-A) or (I-B)), verbascoside +((I-A) or (I-B)), MGK 264 +((I-A) or (I-B)), piperonyl butoxide +((I-A) or (I-B)), piprotal +((I-A) or (I-B)), propyl isomer +((I-A) or (I-B)),S421 + ((I - A) or (I - B)), Sesamex + ((I - A) or (I - B)), Sesasorin + ((I - A) or (I - B)), Sulfoxide + ((I - A) or (I - B)), Anthraquinone + ((I - A) or (I - B)), Copper Naphthenate + ((I - A) or (I - B)), Cupric Oxychloride + ((I - A) or (I - B)), Dicyclopentadiene + ((I - A) or (I - B)), Thiram + ((I - A) or (I - B)), Zinc Naphthenate + ((I - A) or (I - B)), Dithiram + ((I - A) or (I - B)), Imanine + ((I - A) or (I - B)), Ribavirin + ((I - A) or (I - B)), Mercury(II) Oxide + ((I - A) or (I - B)), Thiophanate - Methyl + ((I - A) or (I - B)), Azaconazole + ((I - A) or (I - B)), Bitertanol + ((I - A) or (I - B)), Bromoconazole + ((I - A) or (I - B)), Cyproconazole + ((I - A) or (I - B)), Difenoconazole + ((I - A) or (I - B)), Diniconazole + ((I - A) or (I - B)), Epoxiconazole + ((I - A) or (I - B)), Fenbuconazole + ((I - A) or (I - B)), Flusilazole + ((I - A) or (I - B)), Flutriafol + ((I - A) or (I - B)), Flutriafol + ((I - A) or (I - B)), Hexaconazole + ((I - A) or (I - B)), Imazalil + ((I - A) or (I - B)), Imibenconazole + ((I - A) or (I - B)), Iproconazole + ((I - A) or (I - B)), Metconazole + ((I - A) or (I - B)), Microbutanyl + ((I - A) or (I - B)), Paclobutrazol + ((I - A) or (I - B)), Pefurazoate + ((I - A) or (I - B)), Penconazole + ((I - A) or (I - B)), Prothioconazole + ((I - A) or (I - B)), Pyriofenox + ((I - A) or (I - B)), Prochloraz + ((I - A) or (I - B)), Propiconazole + ((I - A) or (I - B)), Pyrisoxazole + ((I - A) or (I - B)), Simeconazole + ((I - A) or (I - B)), Tebuconazole + ((I - A) or (I - B)),Tetraconazole + ((I-A) or (I-B)), Triadimefon + ((I-A) or (I-B)), Triadimenol + ((I-A) or (I-B)), Triflumizole + ((I-A) or (I-B)), Triticonazole + ((I-A) or (I-B)), Ancymidol + ((I-A) or (I-B)), Fenarimol + ((I-A) or (I-B)), Nuarimol + ((I-A) or (I-B)), Bupirimate + ((I-A) or (I-B)), Dimethirimol + ((I-A) or (I-B)), Ethirimol + ((I-A) or (I-B)), Dodemorph + ((I-A) or (I-B)), Fenpropizine + ((I-A) or (I-B)), Fenpropimorph + ((I-A) or (I-B)), Spiroxamine + ((I-A) or (I-B)), Tridemorph + ((I-A) or (I-B)), Cyprodinil + ((I-A) or (I-B)), Mepanipyrim + ((I-A) or (I-B)), Pyrimethanil + ((I-A) or (I-B)), Fenpiclonil + ((I-A) or (I-B)), Fluazinam + ((I-A) or (I-B)), Benalaxyl + ((I-A) or (I-B)), Furalaxyl + ((I-A) or (I-B)), Metalaxyl-M + ((I-A) or (I-B)), R Metalaxyl + ((I-A) or (I-B)), Ofurace + ((I-A) or (I-B)), Oxadixyl + ((I-A) or (I-B)), Carbendazim + ((I-A) or (I-B)), Diethofencarb + ((I-A) or (I-B)), Fuberidazole + ((I-A) or (I-B)), Thiabendazole + ((I-A) or (I-B)), Chlorothalonil + ((I-A) or (I-B)), Dicloromezine + ((I-A) or (I-B)), Microzole + ((I-A) or (I-B)), Procymidone + ((I-A) or (I-B)), Vinclozolin + ((I-A) or (I-B)), Boscalid + ((I-A) or (I-B)), Carboxin + ((I-A) or (I-B)), Fenfluram + ((I-A) or (I-B)), Flutolanil + ((I-A) or (I-B)), Mepronil + ((I-A) or (I-B)), Oxacarbine + ((I-A) or (I-B)), Penthiopyrad + ((I-A) or (I-B)), Tifluzamide + ((I-A) or (I-B)),Dodine + ((I-A) or (I-B)), Iminoctadin + ((I-A) or (I-B)), Azoxystrobin + ((I-A) or (I-B)), Dimoxystrobin + ((I-A) or (I-B)), Enestroburin + ((I-A) or (I-B)), Fenaminstrobin + ((I-A) or (I-B)), Fluopicoxystrobin + ((I-A) or (I-B)), Fluxapyroxad + ((I-A) or (I-B)), Kresoxim-methyl + ((I-A) or (I-B)), Metominostrobin + ((I-A) or (I-B)), Trifloxystrobin + ((I-A) or (I-B)), Orysastrobin + ((I-A) or (I-B)), Picoxystrobin + ((I-A) or (I-B)), Pyraclostrobin + ((I-A) or (I-B)), Pyrametostrobin + ((I-A) or (I-B)), Pyraoxystrobin + ((I-A) or (I-B)), Ferbam + ((I-A) or (I-B)), Mancozeb + ((I-A) or (I-B)), Maneb + ((I-A) or (I-B)), Metiram + ((I-A) or (I-B)), Propineb + ((I-A) or (I-B)), Zineb + ((I-A) or (I-B)), Captan + ((I-A) or (I-B)), Fluorimide + ((I-A) or (I-B)), Folpet + ((I-A) or (I-B)), Triflumide + ((I-A) or (I-B)), Bordeaux mixture + ((I-A) or (I-B)), Copper oxide + ((I-A) or (I-B)), Mancopper + ((I-A) or (I-B)), Copper oxine + ((I-A) or (I-B)), Nitrotal-isopropyl + ((I-A) or (I-B)), Edifenphos + ((I-A) or (I-B)), Iprobenfos + ((I-A) or (I-B)), Phosphodiphen + ((I-A) or (I-B)), Tolclofos-methyl + ((I-A) or (I-B)), Anilazine + ((I-A) or (I-B)), Benfuracarb + ((I-A) or (I-B)), Blasticidin-S + ((I-A) or (I-B)), Chloroneb + ((I-A) or (I-B)), Chlorothalonil + ((I-A) or (I-B)), Cyflufenamid + ((I-A) or (I-B)), Cymoxanil + ((I-A) or (I-B)),Cyclobutrifluram + ((I - A) or (I - B)), Diclocymet + ((I - A) or (I - B)), Dichlozoline + ((I - A) or (I - B)), Dicloran + ((I - A) or (I - B)), Diethofencarb + ((I - A) or (I - B)), Dimethomorph + ((I - A) or (I - B)), Flumorph + ((I - A) or (I - B)), Dithianon + ((I - A) or (I - B)), Ethaboxam + ((I - A) or (I - B)), Ethirimol + ((I - A) or (I - B)), Famoxadone + ((I - A) or (I - B)), Fenamidone + ((I - A) or (I - B)), Phenoxanil + ((I - A) or (I - B)), Ferimzone + ((I - A) or (I - B)), Fluazinam + ((I - A) or (I - B)), Fluopicolide + ((I - A) or (I - B)), Flusulfamide + ((I - A) or (I - B)), Fluoxapipoxad + ((I - A) or (I - B)), Fenhexamid + ((I - A) or (I - B)), Phosphorous acid, aluminum salt + ((I - A) or (I - B)), Hymexazol + ((I - A) or (I - B)), Iprovalicarb + ((I - A) or (I - B)), Cyazofamid + ((I - A) or (I - B)), Metasulfocarb + ((I - A) or (I - B)), Metrafenone + ((I - A) or (I - B)), Pencycuron + ((I - A) or (I - B)), Phthalide + ((I - A) or (I - B)), Polyoxins + ((I - A) or (I - B)), Propamocarb + ((I - A) or (I - B)), Pyribencarb + ((I - A) or (I - B)), Proquinazid + ((I - A) or (I - B)), Pyroquilon + ((I - A) or (I - B)), Pyriofenone + ((I - A) or (I - B)), Quinoxyfen + ((I - A) or (I - B)), Quintozene + ((I - A) or (I - B)), Thiadiazinyl + ((I - A) or (I - B)), Triazoxide + ((I - A) or (I - B)), Tricyclazole + ((I - A) or (I - B)), Tolyfluanid + ((I - A) or (I - B)), Validamycin + ((I - A) or (I - B)), Valifenalate + ((I - A) or (I - B)), Zoxamide + ((I - A) or (I - B)), Mandipropamid + ((I - A) or (I - B)),Full venteram + ((I - A) or (I - B)), isopyrazam + ((I - A) or (I - B)), sedaxane + ((I - A) or (I - B)), benzobindiflu pyr + ((I - A) or (I - B)), pidiflumetofen + ((I - A) or (I - B)), 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2, ,4-triazol-1-yl)propanoate + ((I-A) or (I-B)), methyl 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1,2,4-triazol-1-ylmethyl)cyclopentanecarboxylate + ((I-A) or (I-B)), 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid (3’,4’,5’-trifluoro-biphenyl-2-yl)-amide + ((I-A) or (I-B)), isoflurprim + ((I-A) or (I-B)), isothianil + ((I-A) or (I-B)), diphenamidtron + ((I-A) or (I-B)), 6-ethyl-5,7-dioxo-pyrrolo[4,5][1,4]dithieno[1,2-c]isothiazole-3-carbonitrile + ((I-A) or (I-B)), 2-(difluoromethyl)-N-[3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide + ((I-A) or (I-B)), 4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine-3-carbonitrile + ((I-A) or (I-B)), (R)-3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide + ((I-A) or (I-B)), 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazol-3-amine + ((I-A) or (I-B)), 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine + ((I-A) or (I-B)), fluindapyril + ((I-A) or (I-B)), kresoxim-methyl (jiaxiangjunzhi) + ((I-A) or (I-B)), rubenmixinanan + ((I-A) or (I-B)), diclobentiazox + ((I-A) or (I-B)), mandestrobin + ((I-A) or (I-B)), 3-(4,4-difluoro-3,4-dihydro-3,3-dimethylisoquinolin-1-yl)quinolone + ((I-A) or (I-B)), 2-[2-fluoro-6-[(8-fluoro-2-methyl-3-quinolyl)oxy]phenyl]propan-2-ol + ((I-A) or (I-B)), oxathiapiprolin + ((I-A) or (I-B)), tert-butyl N-[6-[[[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate + ((I-A) or (I-B)), pyraziflumid + ((I-A) or (I-B)), imidacloprid + ((I-A) or (I-B)), thuriprocarb + ((I-A) or (I-B)), mefenoxazol + ((I-A) or (I-B)), ipconazole + ((I-A) or (I-B)), 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide + ((I-A) or (I-B)), N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methyl-formamidine + ((I-A) or (I-B)), N'-[4-(4,5-dichlorothiazol-2-yl)oxy-2,5-dimethylphenyl]-N-ethyl-N-methyl-formamidine + ((I-A) or (I-B)), [2-[3-[2-[1-[2-[3,5-bis(difluoromethyl)pyrazol-1-yl]acetyl]-4-piperidyl]thiazol-4-yl]-4,5-dihydroisoxazol-5-yl]-3-chloro-phenyl]methanesulfonic acid + ((I-A) or (I-B)), but-3-ynyl N-[6-[[(Z)-[(1-methyltetrazol-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate + ((I-A) or (I-B)), methyl N-[[5-[4-(2,4-dimethylphenyl)triazol-2-yl]-2-methylphenyl]methyl]carbamate + ((I-A) or (I-B)), 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine + ((I-A) or (I-B)), pyridachlormethyl + ((I-A) or (I-B)), 3-(difluoromethyl)-1-methyl-N-[1,1,3-Trimethylinden-4-yl]pyrazole-4-carboxamide + ((I-A) or (I-B)), 1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methyl-phenyl]-4-methyl-tetrazol-5-one + ((I-A) or (I-B)), 1-methyl-4-[3-methyl-2-[[2-methyl-4-(3,4,5-trimethylpyrazol-1-yl)phenoxy]methyl]phenyl]tetrazol-5-one + ((I-A) or (I-B)), aminopyrifen + ((I-A) or (I-B)), ametoctradin + ((I-A) or (I-B)), amisulbrom + ((I-A) or (I-B)), penflufen + ((I-A) or (I-B)), (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-penta-3-enamide + ((I-A) or (I-B)), florylpicoxamid + ((I-A) or (I-B)), fenpicoxamid + ((I-A) or (I-B)), tebufloquin + ((I-A) or (I-B)), ipuphenoxine + ((I-A) or (I-B)), quinofumelin + ((I-A) or (I-B)), isophenamid + ((I-A) or (I-B)), N-[2-[2,4-dichloro-phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide + ((I-A) or (I-B)), N-[2-[2-chloro-4-(trifluoromethyl)phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide + ((I-A) or (I-B)), benzothiostrobin + ((I-A) or (I-B)), fenamacril + ((I-A) or (I-B)), 5-amino-1,3,4-thiadiazole-2-thiol zinc salt (2:1) + ((I-A) or (I-B)), fluopyram + ((I-A) or (I-B)), fluthianil + ((I-A) or (I-B)), fluopyrimid + ((I-A) or (I-B)), pyrapropion + ((I-A) or (I-B)), picarbutrazox + ((I-A) or (I-B)), 2-(difluoromethyl)-N-(3-ethyl-1,1-Dimethyl-inden-4-yl)pyridine-3-carboxamide + ((I-A) or (I-B)), 2-(Difluoromethyl)-N-((3R)-1,1,3-trimethylinden-4-yl)pyridine-3-carboxamide + ((I-A) or (I-B)), 4-[[6-[2-(2,4-Difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + ((I-A) or (I-B)), Methyltetraprol + ((I-A) or (I-B)), 2-(Difluoromethyl)-N-((3R)-1,1,3-trimethylinden-4-yl)pyridine-3-carboxamide + ((I-A) or (I-B)), α-(1,1-Dimethylethyl)-α-[4’-(trifluoromethoxy)[1,1’-biphenyl]-4-yl]-5-pyrimidinemethanol + ((I-A) or (I-B)), Fluoxapiprolin + ((I-A) or (I-B)), Enoxastrobin + ((I-A) or (I-B)), 4-[[6-[2-(2,4-Difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + ((I-A) or (I-B)), 4-[[6-[2-(2,4-Difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-sulfanyl-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + ((I-A) or (I-B)), 4-[[6-[2-(2,4-Difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + ((I-A) or (I-B)), TrinexaPack + ((I-A) or (I-B)), Kummoxastrobin + ((I-A) or (I-B)), Chongshengmycin + ((I-A) or (I-B)), Copper thiodiazole + ((I-A) or (I-B)), Zinc thiazole + ((I-A) or (I-B)), Abamectin + ((I-A) or (I-B)), Iprodione + ((I-A) or (I-B)), N-Octyl-N’-[2-(octylamino)ethyl]ethane-1,2-diamine + ((I-A) or (I-B)); N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine + ((I-A) or (I-B)), N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine + ((I-A) or (I-B)), N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine + ((I-A) or (I-B)), N'-[5-chloro-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine + ((I-A) or (I-B)), N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidine + ((I-A) or (I-B)) (these compounds can be prepared from the methods described in International Publication No. 2015 / 155075); N'-[5-bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine + ((I-A) or (I-B)) (this compound can be prepared from the methods described in IPCOM000249876D); N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenyl-ethyl)phenyl]-N-methyl-formamidine + ((I-A) or (I-B)), N'-[4-(1-cyclopropyl-2,2,(2-Trifluoro-1-hydroxy-ethyl)-5-methoxy-2-methyl-phenyl]-N-isopropyl-N-methyl-formamidine + ((I-A) or (I-B)) (These compounds can be prepared from the methods described in International Publication No. 2018 / 228896); N-ethyl-N'-[5-methoxy-2-methyl-4-[2-trifluoromethyl)oxetan-2-yl]phenyl]-N-methyl-formamidine + ((I-A) or (I-B)), N-ethyl-N'-[5-methoxy-2-methyl-4-[2-trifluoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methyl-formamidine + ((I-A) or (I-B)) (These compounds can be prepared from the methods described in International Publication No. 2019 / 110427); N-[(1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide + ((I-A) or (I-B)), N-[(1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide + ((I-A) or (I-B)), N-[(1R)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide + ((I-A) or (I-B)), N-[(1S)-1-ben, Zir-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide + ((I-A) or (I-B)), N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide + ((I-A) or (I-B)), N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide + ((I-A) or (I-B)), 8-fluoro-N-[(1R)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide + ((I-A) or (I-B)), 8-fluoro-N-[(1S)-1-[(3-fluorophenyl)methyl]-1,3-dimethyl-butyl]quinoline-3-carboxamide + ((I-A) or (I-B)), N-[(1R)-1-benzyl-1,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide + ((I-A) or (I-B)), N-[(1S)-1-benzyl-1,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide + ((I-A) or (I-B)), N-((1R)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide + ((I-A) or (I-B)), N-((1S)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3-carboxamide + ((I-A) or (I-B)) (These compounds can be prepared from the methods described in International Publication No. WO 2017 / 153380);1-(6,7-Dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline + ((I-A) or (I-B)), 1-(6,7-Dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,6-trifluoro-3,3-dimethyl-isoquinoline + ((I-A) or (I-B)), 4,4-Difluoro-3,3-dimethyl-1-(6-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline + ((I-A) or (I-B)), 4,4-Difluoro-3,3-dimethyl-1-(7-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline + ((I-A) or (I-B)), 1-(6-Chloro-7-methyl-pyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline + ((I-A) or (I-B)) (these compounds can be prepared from the methods described in International Publication No. WO 2017 / 025510); 1-(4,5-Dimethylbenzimidazol-1-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline + ((I-A) or (I-B)), 1-(4,5-Dimethylbenzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline + ((I-A) or (I-B)), 6-Chloro-4,4-difluoro-3,3-dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline + ((I-A) or (I-B)), 4,4-Difluoro-1-(5-fluoro-4-methyl-benzimidazol-1-yl)-3,3-dimethyl-isoquinoline + ((I-A) or (I-B)), 3-(4,4-Difluoro-3,3-dimethyl-1-isoquinolyl)-7,8-dihydro-6H-cyclopenta[e]benzimidazole + ((I-A) or (I-B)) (these compounds can be prepared from the methods described in International Publication No. WO 2016 / 156085);N-Ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide + ((I-A) or (I-B)), 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea + ((I-A) or (I-B)), 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea + ((I-A) or (I-B)), 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea + ((I-A) or (I-B)), N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide + ((I-A) or (I-B)), 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one + ((I-A) or (I-B)), 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one + ((I-A) or (I-B)), ethyl 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrazole-4-carboxylate + ((I-A) or (I-B)), N,N-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-1,2,4-triazol-3-amine + ((I-A) or (I-B)). The compounds in this paragraph can be prepared from the methods described in International Publication No. WO 2017 / 055473, International Publication No. WO 2017 / 055469, International Publication No. WO 2017 / 093348 and International Publication No. WO 2017 / 118689; 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol + ((I-A) or (I-B)) (this compound can be prepared from the method described in International Publication No. WO 2017 / 029179);2-[6-(4-Bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol + ((I-A) or (I-B)) (This compound can be prepared from the method described in International Publication No. WO 2017 / 029179); 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile + ((I-A) or (I-B)) (This compound can be prepared from the method described in International Publication No. WO 2016 / 156290); 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile + ((I-A) or (I-B)) (This compound can be prepared from the method described in International Publication No. WO 2016 / 156290); (4-Phenoxyphenyl)methyl 2-amino-6-methyl-pyridine-3-carboxylate + ((I-A) or (I-B)) (This compound can be prepared from the method described in International Publication No. WO 2014 / 006945); 2,6-Dimethyl-1H,5H-[1,4]dithiino[2,3-c:5,6-c’]dipyrrole-1,3,5,7(2H,6H)-tetrone + ((I-A) or (I-B)) (This compound can be prepared from the method described in International Publication No. WO 2011 / 138281); N-Methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide + ((I-A) or (I-B)); N-Methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + ((I-A) or (I-B)); (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-penta-3-enamide + ((I-A) or (I-B)) (This compound can be prepared from the method described in International Publication No. WO 2018 / 153707); N’-(2-chloro-5-methyl-4-phenoxy-phenyl)-N-ethyl-N-methyl-formamidine + ((I-A) or (I-B));N’-[2-chloro-4-(2-fluorophenoxy)-5-methyl-phenyl]-N-ethyl-N-methyl-formamidine + ((I-A) or (I-B)) (This compound can be prepared from the method described in International Publication No. WO 2016 / 202742); 2-(difluoromethyl)-N-[(3S)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide + ((I-A) or (I-B)) (This compound can be prepared from the method described in International Publication No. WO 2014 / 095675); (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone + ((I-A) or (I-B)), (3-methylisoxazol-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanone + ((I-A) or (I-B)) (These compounds can be prepared from the method described in International Publication No. WO 2017 / 220485); 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide + ((I-A) or (I-B)) (This compound can be prepared from the method described in International Publication No. WO 2018 / 065414); ethyl 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylate + ((I-A) or (I-B)) (This compound can be prepared from the method described in International Publication No. WO 2018 / 158365);2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide + ((I-A) or (I-B)), N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + ((I-A) or (I-B)), N-[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + ((I-A) or (I-B)), N-[N-methoxy-C-methyl-carboximidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide + ((I-A) or (I-B)) (these compounds can be prepared from the methods described in WO 2018 / 202428), chloro-inconazide + ((I-A) or (I-B)), flumetylsulforim + ((I-A) or (I-B)), fluoxythioconazole + ((I-A) or (I-B)), flufenoxadiazam + ((I-A) or (I-B)), metallyl picoxamide + ((I-A) or (I-B));1-[1-(4-Chlorophenyl)cyclobutyl]ethyl (2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)-amino]propanoate + ((I-A) or (I-B)), [2-(4-bromo-7-fluoro-indol-1-yl)-1-methyl-propyl] (2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate + ((I-A) or (I-B)), [2-(3,5-dichloro-2-pyridyl)-1-methyl-propyl] (2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate + ((I-A) or (I-B)), [(1S)-1-[1-(1-naphthyl)cyclopropyl]ethyl] (2S)-2-[[3-(acetoxymethoxy)-4-methoxy-pyridine-2-carbonyl]amino]propanoate + ((I-A) or (I-B)), [(1S)-1-[1-(1-naphthyl)cyclopropyl]ethyl] (2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate + ((I-A) or (I-B)), [2-[[(1S)-2-[2-(3,5-dichloro-2-pyridyl)-1-methyl-propo; [[4-methoxy-3-pyridyl]oxymethyl 2-methylpropanoate + ((I-A) or (I-B)) with [[(1S)-1-methyl-2-oxo-ethyl]carbamoyl]-, [4-methoxy-2-[[(1S)-1-methyl-2-[(1S)-1-[1-(1-naphthyl)cyclopropyl]ethoxy]-2-oxo-ethyl]carbamoyl]-3-pyridyl]oxymethyl 2-methylpropanoate + ((I-A) or (I-B)), [2-(4-bromophenyl)-1,2-dimethyl-propyl] (2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate + ((I-A) or (I-B)), 1-(1-phenylcyclohexyl)ethyl (2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate + ((I-A) or (I-B)), [1-methyl-2-(2-quinolyl)propyl] (2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate + ((I-A) or (I-B)), [2-(7-bromoindol-1-yl)-1-methyl-propyl] (2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate + ((I-A) or (I-B)), [1-methyl-2-[6-(trifluoromethyl)indol-1-yl]propyl] (2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate + ((I-A) or (I-B)), (2-indazol-1-yl-1-methyl-propyl) (2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate + ((I-A) or (I-B)), [2-(5-chloro-2-thienyl)-1-methyl-propyl] (2S)-2-[(3-hydroxy-4-methoxy-pyridine-2-carbonyl)amino]propanoate + ((I-A) or (I-B)), [2-(4,(2S)-2-[(3-acetoxy-4-methoxypyridine-2-carbonyl)amino]propanoate of (7-dichloroindol-1-yl)-1-methylpropyl + ((I-A) or (I-B)), (2S)-2-[(3-acetoxy-4-methoxypyridine-2-carbonyl)amino]propanoate of [2-(7-bromo-4-fluoroindol-1-yl)-1-methylpropyl] + ((I-A) or (I-B)), (2S)-2-[(3-acetoxy-4-methoxypyridine-2-carbonyl)amino]propanoate of [(1S)-1-[1-(1-naphthyl)cyclopropyl]ethyl] + ((I-A) or (I-B)) (these compounds can be prepared by the method described in International Publication No. 2020 / 208096); methyl N-[[5-[1-(2,6-difluoro-4-isopropylphenyl)pyrazol-3-yl]-2-methylphenyl]methyl]carbamate + ((I-A) or (I-B)), methyl N-[[5-[1-(4-cyclopropyl-2,6-difluorophenyl)pyrazol-3-yl]-2-methylphenyl]methyl]carbamate + ((I-A) or (I-B)), (2E)-2-methoxyimino-N-methyl-2-[3-methyl-2-[[(E)-1-[4-(trifluoromethyl)-2-pyridyl]ethylideneamino]oxymethyl]phenyl]acetamide + ((I-A) or (I-B)), 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(2,4-dimethylphenyl)-2,2-difluoroethyl]-5-methyl-pyridazine-4-carboxamide + ((I-A) or (I-B)), 6-chloro-N-[2-(2-chloro-4-methylphenyl)-2,2-difluoroethyl]-3-(3-cyclopropyl-2-fluorophenoxy)-5-methyl-pyridazine-4-carboxamide + ((I-A) or (I-B)), 6-chloro-3-(3-cyclopropyl-2-fluorophenoxy)-N-[2-(3,4-dimethylphenyl)-2,2-difluoroethyl]-5-methyl-pyridazine-4-carboxamide + ((I-A) or (I-B)), 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-(Difluorophenyl)ethyl]pyrimidin-2-amine + ((I-A) or (I-B)), 2-(Difluoromethyl)-5-[2-[1-(2,6-difluorophenyl)cyclopropoxy]pyrimidin-5-yl]-1,3,4-oxadiazole + ((I-A) or (I-B)), 5-[5-(Difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)cyclopropyl]pyrimidin-2-amine + ((I-A) or (I-B)), 5-[5-(Difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)cyclopropyl]pyrimidin-2-amine + ((I-A) or (I-B)), N-[1-(2-fluorophenyl)cyclopropyl]-5-[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]pyrimidin-2-amine + ((I-A) or (I-B)), 5-[5-(Difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)ethyl]pyrimidin-2-amine + ((I-A) or (I-B)), 5-[5-(Difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(3,5-difluorophenyl)ethyl]pyrimidin-2-amine + ((I-A) or (I-B)), Ethyl 1-[[4-[[2-(trifluoromethyl)-1,3-dioxolan-2-yl]methoxy]phenyl]methyl]-1H-pyrazole-4-carboxylate + ((I-A) or (I-B)), Ethyl 1-[[4-[[(1Z)-2-ethoxy-3,3,3-trifluoro-1-propen-1-yl]oxy]phenyl]methyl]-1H-pyrazole-4-carboxylate + ((I-A) or (I-B)), 3-[[3-chloro-2-(2-ethylpyrazol-3-yl)phenyl]methyl]-7,8-difluoro-2-methyl-quinoline + ((I-A) or (I-B)), N-[2-(2-ethylpyrazol-3-yl)phenyl]-5,6-difluoro-3-methyl-quinoxalin-2-amine + ((I-A) or (I-B)), 5,6-Difluoro-N-[3-fluoro-2-(2-propylpyrazol-3-yl)phenyl]-3-methyl-quinoxalin-2-amine + ((I-A) or (I-B)), N-[3-chloro-2-(2-propylpyrazol-3-yl)phenyl]-7,8-difluoro-2-methyl-quinolin-3-amine + ((I-A) or (I-B)), 1-(5,6-dimethyl-3-pyridyl)-4,4-difluoro-3,3-dimethyl-isoquinoline + ((I-A) or (I-B)), 1-[6-(difluoromethyl)-5-methyl-3-pyridyl]-4,4-difluoro-3,3-dimethyl-isoquinoline + ((I-A) or (I-B)), methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoate + ((I-A) or (I-B)) and 2-(1-chlorocyclopropyl)-1-(2-chlorophenyl)-3-(1,2,4-triazol-1-yl)propan-2-ol + ((I-A) or (I-B)).,

[0218] References enclosed in square brackets that follow the active ingredient, e.g., [3878-19-1], refer to Chemical Abstracts Registry Numbers. The above-mentioned mixing partners are known. If the active ingredients are listed in “The Pesticide Manual” [The Pesticide Manual - A World Compendium; Thirteenth Edition; Editor: C.D.S. Tomlin; The British Crop Protection Council], they are listed therein under the entry numbers given in square brackets above for the specific compounds; for example, the compound “abamectin” is listed under entry number (1). If “[CCN]” is added to a specific compound as above, the said compound is listed in the “Compendium of Pesticide Common Names” accessible on the Internet [A. Wood; Compendium of Pesticide Common Names, Copyright (R) 1995 - 2004]; for example, the compound “acetoprole” is described at the Internet address http: / / www.alanwood.net / pesticides / acetoprole.html.

[0219] Most of the active ingredients described above are referred to by their so-called “common names” where, in each case, the relevant “ISO common name” or another “common name” is used. If the name is not a “common name”, the nature of the name used instead is given enclosed in square brackets for the specific compound; in that case, the IUPAC name, IUPAC / Chemical Abstracts name, “chemical name”, “trivial name”, “compound name” or “development code” is used, or, if none of these names are used and no “common name” is used either, an “alternative name” is utilized. The “CAS Registry Number” means the Chemical Abstracts Registry Number.

[0220] The active ingredient mixture of the polymorphs of the present invention preferably has a mixing ratio of 100:1 to 1:100, particularly 50:1 to 1:50, more particularly 20:1 to 1:20, more particularly 10:1 to 1:10, and even more particularly 5:1 to 1:5, and these mixing ratios are based on weight.

[0221] In another aspect of the present invention, there is provided a bactericidal and fungicidal composition comprising a mixture of a polymorph (I-A) or (I-B) according to the first or second aspect as component (A) and a component (B) as an active ingredient, wherein component (A) is selected from a polymorph of a compound of formula (I-A) or a polymorph of a compound of formula (I-B), and component (B) is benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, sedaxane, bixafen, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, propiconazole, epoxiconazole, metconazole, tetraconazole, fluoxastrobin, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanate, methyl 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1,2,(4-triazol-1-ylmethyl)cyclopentanecarboxylate, flutriafol, mefenoxam, ipconazole, paclobutrazol, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, metalaxyl-M, fenpropidin, fenpropimorph, cyprodinil, spiroxamine, mancozeb, chlorothalonil, phosetyl-aluminum, acibenzolar-S-methyl, enestrobin, fluopyram, fluxapyroxad, isoflucypram, methyltetraprole, florylpicoxamid, mefentrifluconazole, metalylpicoxamid, flufioxazin, isfetamid, procymidone, carbendazim, fenhexamid, prochloraz, prohexadione-calcium, tea tree oil (extract of the Melaleuca alternifolia plant, commercially available as Timorex Gold®, a broad-spectrum, plant-derived biocidal and fungicidal agent), N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methylformamidine, cyclobutrifluram calcium phosphonate, cis-jasmone, trinexapac-ethyl, glyphosate, 2,4-D (2,4-dichlorophenoxyacetic acid) or thiamethoxam, or a salt, enantiomer, tautomer or N-oxide thereof, is a compound selected from the group consisting of.,

[0222] Generally, the weight ratio of component (A) to component (B) can be from 1000:1 to 1:1000, from 100:1 to 1:100, preferably from 50:1 to 1:50, more preferably from 20:1 to 1:40, even more preferably from 15:1 to 1:30, even more preferably from 12:1 to 1:25, or from 10:1 to 1:20, or from 10:1 to 1:10, or from 5:1 and 1:15, or from 5:1 to 1:5, or from 4:1 to 1:4, or from 3:1 to 1:10, or from 3:1 to 1:3, or from 2:1 to 1:5, or 1:1.

[0223] In a preferred composition according to this aspect of the present invention, component (A) is a polymorph of N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide (Compound I-A), or a salt, enantiomer, tautomer or N-oxide thereof, and component (B) is benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, sedaxane, bixafen, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, propiconazole, epoxiconazole, metconazole, tetraconazole, fluoxastrobin, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanate, methyl 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1,2,(4-triazol-1-ylmethyl)cyclopentanecarboxylate, flutriafol, mefenoxam, ipconazole, paclobutrazol, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, metalaxyl-M, fenpropidin, fenpropimorph, cyprodinil, spiroxamine, mancozeb, chlorothalonil, folpet, copper oxychloride, copper hydroxide, sulfur, oxathiapiprolin, iprovalicarb, quinoxyfen, mandipropamid, fluazinam, fluazinil, fosetyl-aluminum, acibenzolar-S-methyl, enestrobin, imidacloprid, flupyradifurone, isoflucypram, methyltetraprole, florpyrauxifen, mefentrifluconazole, flufenzin, isophenamid, procymidone, carbendazim, fenhexamid, prochloraz, prohexadione-calcium, tea tree oil (extract of the tea tree plant (Melaluca alternifolia), commercially available as Timorex Gold®, a broad-spectrum biofungicide and biocidal agent derived from plants), N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methylformamidine, cyclobutrifluram calcium phosphonate, cis-jasmone, trinexapac-ethyl, glyphosate, 2,4-D (2,4-dichlorophenoxyacetic acid) or thiamethoxam, or a salt, enantiomer, tautomer or N-oxide thereof, selected from the group consisting of.,

[0224] In another preferred composition according to the present invention, component (A) is a polymorph of N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide (Compound I-B), or a salt, enantiomer, tautomer or N-oxide thereof, and component (B) is benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, sedaxane, bixafen, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, propiconazole, epoxiconazole, metconazole, tetraconazole, fluoxastrobin, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanate, methyl 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1,2,(4-triazol-1-ylmethyl)cyclopentanecarboxylate, flutriafol, mefenoxam, ipconazole, paclobutrazol, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, metalaxyl-M, fenpropidin, fenpropimorph, cyprodinil, spiroxamine, mancozeb, chlorothalonil, folpet, copper oxychloride, copper hydroxide, sulfur, oxathiapiprolin, iprovalicarb, quinoxyfen, mandipropamid, fluazinam, fluoxydinil, fosetyl-aluminum, acibenzolar-S-methyl, enestrobin, imidacloprid, flupyradifurone, isoflucypram, methyltetraprole, florpyrauxifen-benzyl, meptyldinocap, flufenoxdiazin, isfetamid, procymidone, carbendazim, fenhexamid, prochloraz, prohexadione-calcium, tea tree oil (extract of Melaleuca alternifolia, commercially available as Timorex Gold®, a broad-spectrum, plant-derived biocidal and fungicidal agent), N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methylformamidine, cyclobutrifluram calcium phosphonate, cis-jasmone, trinexapac-ethyl, glyphosate, 2,4-D (2,4-dichlorophenoxyacetic acid) or thiamethoxam, or a salt, enantiomer, tautomer or N-oxide thereof, selected from the group consisting of.,

[0225] In any of the compositions according to the present invention, the composition may contain an additional active ingredient component (C) different from component (B), such as methyltetrapol, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, metominostrobin, prothioconazole, cyproconazole, difenoconazole, tebuconazole, propiconazole, epoxiconazole, hexaconazole, mefentrifluconazole, metconazole, benzovindiflupyr, pidiflumetofen, fluopyroxad, sedaxane, bixafen, isopyrazam, fluopyram, fluindapyr, isoflupiprolam, ipfentrifluconazole, quinofumelin, iprovalicarb, aminopyrifen, fluazinam, fluazinilam, fenpicoxamid, florpyrauxamid, fenpropidin, fenpropimorph, mancozeb, chlorothalonil, cyclobutrifluram, copper oxychloride, copper hydroxide, N’-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine), N’-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine, N’-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine, N’-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidine, N’-[5-chloro-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N’-(2-chloro-5-methyl-4-phenoxyphenyl)-N-ethyl-N-methyl-formamidine, N’-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methyl-formamidine, N’-[2-chloro-4-(3-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methyl-formamidine, N’-(2-bromo-5-methyl-4-phenoxyphenyl)-N-ethyl-N-methyl-formamidine,N’-[2-Bromo-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methyl-formamidine, N’-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-isopropyl-N-methyl-formamidine, N’-[4-(2-cyanophenoxy)-2-methyl-5-(trifluoromethyl)phenyl]-N-ethyl-N-methyl-formamidine, N’-[5-bromo-2-methyl-4-(2-methylphenoxy)phenyl]-N-ethyl-N-methyl-formamidine, N-ethyl-N’-[4-(2-fluorophenoxy)-2-methyl-5-(trifluoromethyl)phenyl]-N-methyl-formamidine, (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-penta-3-enamide, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-penta-3-enamide, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, methyl 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1,2,4-triazol-1-ylmethyl)cyclopentanecarboxylate, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide,Selected from the group consisting of N-[N-methoxy-C-methyl-carboximidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, N-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]cyclopropanecarboxamide, N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, 1-(5,6-dimethyl-3-pyridyl)-4,4-difluoro-3,3-dimethyl-isoquinoline and 1-[6-(difluoromethyl)-5-methyl-3-pyridyl]-4,4-difluoro-3,3-dimethyl-isoquinoline.,

[0226] Component (C) compounds are referred to herein and above by their so-called "ISO common name" or other "common name" or trade name used in individual cases. Component (C) compounds are known, commercially available, and / or can be prepared using methods known in the art.,

[0227] In another aspect of the present invention, there is provided a fungicidal and bactericidal composition comprising, as an active ingredient, a mixture of the polymorph (A) and component (B) and component (C) according to the first or second aspect, wherein component (A) is selected from the polymorph of the compound of formula (I-A) or the polymorph of the compound of formula (I-B), and components (B) and (C) are benzovindiflupyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, sedaxane, bixafen, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, propiconazole, epoxiconazole, metconazole, tetraconazole, fluoxastrobin, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoate, methyl 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1,2,(4-triazol-1-ylmethyl)cyclopentanecarboxylate, flutriafol, mefenoxam, ipconazole, paclobutrazol, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, metalaxyl-M, fenpropidin, fenpropimorph, cyprodinil, spiroxamine, mancozeb, chlorothalonil, folpet, copper oxychloride, copper hydroxide, sulfur, oxathiapiprolin, iprovalicarb, quinoxyfen, mandipropamid, fluazinam, fluoxastrobin, fosetyl-aluminum, acibenzolar-S-methyl, enestrobin, imidacloprid, flupyradifurone, isoflucypram, methyltetraprole, florylpicoxamid, metflupyricoxamid, flenoxazadiazam, isfetamid, procymidone, carbendazim, fenhexamid, prochloraz, prohexadione-calcium, tea tree oil (extract of Melaleuca alternifolia, commercially available as Timorex Gold® and a broad-spectrum biofungicide and biocide derived from plants), N’-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methylformamidine, cyclobutrifluram calcium phosphonate, cis-jasmone, trinexapac-ethyl, glyphosate, 2,4-D (2,4-dichlorophenoxyacetic acid) or thiamethoxam, or a salt, enantiomer, tautomer or N-oxide thereof, provided that components (B) and (C) are not the same compound.,

[0228] In a preferred composition according to this aspect of the present invention, component (A) is a polymorph of N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide (Compound I-A), or a salt, enantiomer, tautomer or N-oxide thereof, and components (B) and (C) are benzobin diflu pyr, flu pyraoxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, sedaxane, bixafen, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, propiconazole, epoxiconazole, metconazole, tetraconazole, fluoxythioconazole, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propan oate, methyl 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1,2,(4-triazol-1-ylmethyl)cyclopentanecarboxylate, flutriafol, mefenoxam, ipconazole, paclobutrazol, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, metalaxyl-M, fenpropidin, fenpropimorph, cyprodinil, spiroxamine, mancozeb, chlorothalonil, phosetyl-aluminum, acibenzolar-S-methyl, enestrobin, ipfencarbazide, fluindapyr, isoflurprim, methyltetraprole, florylpicoxamid, metflupyricoxamid, flufenoxazadim, isophenamid, procymidone, carbendazim, fenhexamid, prochloraz, prohexadione-calcium, tea tree oil (extract of the Melaleuca alternifolia plant, commercially available as Timorex Gold®, a broad-spectrum, plant-derived biocidal and fungicidal agent), N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methylformamidine, cyclobutrifluram calcium phosphonate, cis-jasmone, trinexapac-ethyl, glyphosate, 2,4-D (2,4-dichlorophenoxyacetic acid) or thiamethoxam, or a salt, enantiomer, tautomer or N-oxide thereof, provided that components (B) and (C) are not the same compound.,

[0229] In another preferred composition according to this aspect of the present invention, component (A) is a polymorph of N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide (Compound I-B), or a salt, enantiomer, tautomer or N-oxide thereof, and components (B) and (C) are benzobin difluopyr, fluxapyroxad, pydiflumetofen, isopyrazam, fluopyram, penthiopyrad, sedaxane, bixafen, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, propiconazole, epoxiconazole, metconazole, tetraconazole, fluoxythioconazole, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propanoate, methyl 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1,2,(4-triazol-1-ylmethyl)cyclopentanecarboxylate, flutriafol, mefenoxam, ipconazole, paclobutrazol, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, metalaxyl-M, fenpropidin, fenpropimorph, cyprodinil, spiroxamine, mancozeb, chlorothalonil, folpet, copper oxychloride, copper hydroxide, sulfur, oxathiapiprolin, iprovalicarb, quinoxyfen, mandipropamid, fluazinam, fluoxastrobin, fosetyl-aluminum, acibenzolar-S-methyl, enestrobin, pyraclostrobin, fluindapyr, isoflucypram, methyltetraprole, florylpicoxamid, metflupyricoxamid, flufenoxadiazam, isfetamid, procymidone, carbendazim, fenhexamid, prochloraz, prohexadione-calcium, tea tree oil (extract of Melaleuca alternifolia, commercially available as Timorex Gold®, a broad-spectrum, plant-derived biocide and fungicide), N’-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methylformamidine, cyclobutrifluram calcium phosphonate, cis-jasmone, trinexapac-ethyl, glyphosate, 2,4-D (2,4-dichlorophenoxyacetic acid) or thiamethoxam, or a salt, enantiomer, tautomer or N-oxide thereof, provided that components (B) and (C) are not the same compound.,

[0230] Components (B) and (C) may enhance the effectiveness of component (A) against fungi when combined with component (A), and vice versa. Also, the fungicidal and antifungal composition may be effective against a wider range of fungal pathogens than those that can be addressed by individual active ingredients when used alone. Generally, the weight ratio of component (A) to the mixture of components (B) and (C) can be 100:1 to 1:100, or 50:1 to 1:50, or 20:1 to 1:20, or 10:1 to 1:10, or 5:1 and 1:5. Alternatively, the weight ratio of component (A) to the mixture of components (B) and (C) can be 2:1 to 1:2, or 4:1 to 2:1, or 1:1, or 5:1, or 5:2, or 5:3, or 5:4, or 4:1, or 4:2, or 4:3, or 3:1, or 3:2, or 2:1, or 1:5, or 2:5, or 3:5, or 4:5, or 1:4, or 2:4, or 3:4, or 1:3, or 2:3, or 1:2, or 1:600, or 1:300, or 1:150, or 1:35, or 2:35, or 4:35, or 1:75, or 2:75, or 4:75, or 1:6000, or 1:3000, or 1:1500, or 1:350, or 2:350, or 4:350, or 1:750, or 2:750, or 4:750. These mixing ratios are understood to include weight ratios on the one hand and molar ratios on the other hand.

[0231] In an embodiment of the present invention where the composition includes component (A), component (B) and component (C), the weight ratio of component (A) to the sum of component (B) and component (C) can be 100:1 to 1:100, preferably 50:1 to 1:50, more preferably 20:1 to 1:40, even more preferably 15:1 to 1:30, even more preferably 12:1 to 1:25, or 10:1 to 1:20, or 10:1 to 1:10, or 5:1 and 1:15, or 5:1 to 1:5, or 4:1 to 1:4, or 3:1 to 1:10, or 3:1 to 1:3, or 2:1 to 1:5, or 1:1.

[0232] In a preferred embodiment of the present invention, the polymorph of the compound of formula (I-A) or (I-B) according to the present invention can be mixed with one or more additional active ingredients selected from component (B), wherein said component (B) is methyltetrapole, azoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, metominostrobin, prothioconazole, cyproconazole, difenoconazole, tebuconazole, propiconazole, epoxiconazole, hexaconazole, mefentrifluconazole, metconazole, benzovindiflupyr, pidiflumetofen, fluxapyroxad, sedaxane, bixafen, isopyrazam, fluopyram, fluindapyr, isoflurprim, ipfencarbazone, quinofumelin, iprovalicarb, aminopyrifen, fluazinam, fluoxastrobin, fenpicoxamid, florylpicoxamid, fenpropidin, fenpropimorph, mancozeb, chlorothalonil, cyclobutrifluram, copper oxychloride, copper hydroxide, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine), N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidine, N'-[5-chloro-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-(2-chloro-5-methyl-4-phenoxyphenyl)-N-ethyl-N-methyl-formamidine, N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methyl-formamidine, N'-[2-chloro-4-(3-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methyl-formamidine,N'-(2-Bromo-5-methyl-4-phenoxyphenyl)-N-ethyl-N-methyl-formamidine, N'-[2-bromo-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methyl-formamidine, N'-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-isopropyl-N-methyl-formamidine, N'-[4-(2-cyanophenoxy)-2-methyl-5-(trifluoromethyl)phenyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-4-(2-methylphenoxy)phenyl]-N-ethyl-N-methyl-formamidine, N-ethyl-N'-[4-(2-fluorophenoxy)-2-methyl-5-(trifluoromethyl)phenyl]-N-methyl-formamidine, (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-penta-3-enamide, (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-penta-3-enamide, 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, methyl 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1,2,4-triazol-1-ylmethyl)cyclopentanecarboxylate, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide, N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide,N-[N-Methoxy-C-methyl-carboximidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, N-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]cyclopropanecarboxamide, N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, 1-(5,6-dimethyl-3-pyridyl)-4,4-difluoro-3,3-dimethyl-isoquinoline, 1-[6-(difluoromethyl)-5-methyl-3-pyridyl]-4,4-difluoro-3,3-dimethyl-isoquinoline, methyl N-[[5-[1-(4-cyclopropyl-2,6-difluoro-phenyl)pyrazol-3-yl]-2-methyl-phenyl]methyl]carbamate (this compound can be prepared from the method described in International Publication No. 2021 / 226234), methyl N-[[5-[1-(2,6-difluoro-4-isopropyl-phenyl)pyrazol-3-yl]-2-methyl-phenyl]methyl]carbamate (this compound can be prepared from the method described in International Publication No. 2021 / 226234) or [(2S,3S)-3-(2-methylphenyl)butan-2-yl](2S)-2-[(4-methoxy-3-propanoyloxypyridine-2-carbonyl)amino]propanoate (metaryl picoxamide, this compound can be prepared from the method described in International Publication No. 2019 / 173665) selected from the group consisting of.,

[0233] Preferably, component (B) is a compound selected from the group consisting of methyltetrapole, azoxystrobin, trifloxystrobin, picoxystrobin, metominostrobin, prothioconazole, cyproconazole, difenoconazole, tebuconazole, propiconazole, mefentrifluconazole, metconazole, benzovindiflupyr, pidiflumetofen, sedaxane, isopyrazam, ipfencarbazone, fluazinam, florylpicoxamid, fenpropidin, mancozeb, chlorothalonil, cyclobutrifluram, copper oxychloride, copper hydroxide, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-chloro-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, methyl N-[[5-[1-(2,6-difluoro-4-isopropyl-phenyl)pyrazol-3-yl]-2-methyl-phenyl]methyl]carbamate (this compound can be prepared by the method described in International Publication No. 2021 / 226234), or [(2S,3S)-3-(2-methylphenyl)butan-2-yl](2S)-2-[(4-methoxy-3-propanoyloxypyridine-2-carbonyl)amino]propanoate (metarhizium picoxystrobin, this compound can be prepared by the method described in International Publication No. 2019 / 173665).

[0234] According to another aspect of the present invention, there is provided a fungicidal and moldicidal composition containing a mixture of components (A) and (B) as active ingredients, wherein component (A) is N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide (Compound I-A), and component (B) is methyltetrapor, azoxystrobin, trifloxystrobin, picoxystrobin, metominostrobin, prothioconazole, cyproconazole, difenoconazole, tebuconazole, propiconazole, mefentrifluconazole, metconazole, benzovindiflupyr, pidiflumetofen, sedaxane, isopyrazam, ipfencarbazone, fluazinam, florylpicoxamid, fenpropimorph, mancozeb, chlorothalonil, cyclobutrifluram, copper oxychloride, copper hydroxide, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-chloro-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, methyl N-[[5-[1-(2,6-difluoro-4-isopropyl-phenyl)pyrazol-3-yl]-2-methyl-phenyl]methyl]carbamate (this compound can be prepared from the method described in International Publication No. 2021 / 226234) or [(2S,3S)-3-(2-methylphenyl)butan-2-yl](2S)-2-[(4-methoxy-3-propanoyloxypyridine-2-carbonyl)amino]propanoate (metarifluconazole, this compound can be prepared from the method described in International Publication No. 2019 / 173665), which is a compound selected from the group consisting of.Preferably, for controlling Phakopsora pachyrhizi in genetically modified soybean plants. In one embodiment, the genetically modified soybean plant is a Bt soybean plant selected from Intacta RR2 PRO® or Conkesta Enlist E3®.

[0235] According to another aspect of the present invention, there is provided a bactericidal and fungicidal composition comprising a mixture of components (A) and (B) as active ingredients, wherein component (A) is N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide (Compound I-B), and component (B) is methyltetraporphyrin, azoxystrobin, trifloxystrobin, picoxystrobin, metominostrobin, prothioconazole, cyproconazole, difenoconazole, tebuconazole, propiconazole, mefentrifluconazole, metconazole, benzovindiflupyr, pidiflumetofen, sedaxane, isopyrazam, ipfencarbazide, fluazinam, florylpicoxamide, fenpropimorph, mancozeb, chlorothalonil, cyclobutrifluram, copper oxychloride, copper hydroxide, N’-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N’-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine, N’-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine, N’-[5-chloro-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, methyl N-[[5-[1-(2,6-difluoro-4-isopropyl-phenyl)pyrazol-3-yl]-2-methyl-phenyl]methyl]carbamate (this compound can be prepared from the method described in International Publication No. 2021 / 226234), or [(2S,3S)-3-(2-methylphenyl)butan-2-yl](2S)-2-[(4-methoxy-3-propanoyloxypyridine-2-carbonyl)amino]propanoate (metariflumetamide, this compound can be prepared from the method described in International Publication No. 2019 / 173665), which is a compound selected from the group consisting of.Preferably, for controlling Phakopsora pachyrhizi in genetically modified soybean plants. In one embodiment, the genetically modified soybean plant is a Bt soybean plant selected from Intacta RR2 PRO® or Conkesta Enlist E3®.

[0236] According to another aspect of the present invention, there is provided a bactericidal and fungicidal composition containing a mixture of components (A) and (B) as active ingredients, wherein component (A) is a polymorph of N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide (Compound I-A), or a salt, enantiomer, tautomer or N-oxide thereof, and component (B) is methyltetraporphyrin, azoxystrobin, trifloxystrobin, picoxystrobin, metominostrobin, prothioconazole, cyproconazole, difenoconazole, tebuconazole, propiconazole, mefentrifluconazole, metconazole, benzovindiflupyr, pidiflumetofen, sedaxane, isopyrazam, ipfbufenpyr, fluazinam, florylpicoxamide, fenpropizine, mancozeb, chlorothalonil, cyclobutrifluram, copper oxychloride, copper hydroxide, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-chloro-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, methyl N-[[5-[1-(2,6-difluoro-4-isopropyl-phenyl)pyrazol-3-yl]-2-methyl-phenyl]methyl]carbamate (this compound can be prepared by the method described in International Publication No. 2021 / 226234), or [(2S,A compound selected from the group consisting of (3S)-3-(2-methylphenyl)butan-2-yl (2S)-2-[(4-methoxy-3-propanoyloxypyridine-2-carbonyl)amino]propanoate (methallyl picoxamide, this compound can be prepared from the method described in International Publication No. 2019 / 173665). Preferably, for controlling Phakopsora pachyrhizi in genetically modified soybean plants. In one embodiment, the genetically modified soybean plant is a Bt soybean plant selected from Intacta RR2 PRO® or Conkesta Enlist E3®.,

[0237] According to another aspect of the present invention, there is provided a fungicidal and moldicidal composition comprising, as an active ingredient, a mixture of components (A) and (B), wherein component (A) is a polymorph of N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide (Compound I-B), or a salt, enantiomer, tautomer or N-oxide (I-B) thereof, and component (B) is methyltetrapor, azoxystrobin, trifloxystrobin, picoxystrobin, metominostrobin, prothioconazole, cyproconazole, difenoconazole, tebuconazole, propiconazole, mefentrifluconazole, metconazole, benzovindiflupyr, pidiflumetofen, sedaxane, isopyrazam, ipfencarbazone, fluazinam, florylpicoxamid, fenpropizine, mancozeb, chlorothalonil, cyclobutrifluram, copper oxychloride, copper hydroxide, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-chloro-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, methyl N-[[5-[1-(2,6-difluoro-4-isopropyl-phenyl)pyrazol-3-yl]-2-methyl-phenyl]methyl]carbamate (this compound can be prepared by the method described in International Publication No. 2021 / 226234), or [(2S,A compound selected from the group consisting of (3S)-3-(2-methylphenyl)butan-2-yl (2S)-2-[(4-methoxy-3-propanoyloxypyridine-2-carbonyl)amino]propanoate (methacrylpicoxamide, which can be prepared by the method described in International Publication No. 2019 / 173665). Preferably, for controlling Phakopsora pachyrhizi in genetically modified soybean plants. In one embodiment, the genetically modified soybean plant is a Bt soybean plant selected from Intacta RR2 PRO® or Conkesta Enlist E3®.,

[0238] Component (B) compounds are referred to herein and above by their so-called "ISO common names" or other "common names" or trade names used in individual cases. Component (B) compounds are known, commercially available, and / or can be prepared using methods known in the art and / or, for example, the methods reported in documents such as International Publication Nos. 2015 / 155075, 2016 / 202742, 2017 / 005710, 2018 / 108977, 2018 / 153707, 2018 / 098216, 2019 / 093522, 2018 / 145921, 2015 / 185485, 2017 / 076742, 2017 / 081311, 2017 / 085100, 2017 / 093019, 2017 / 178245, and 2017 / 211649.

[0239] In an embodiment of the present invention, the composition comprises a polymorph of a compound of formula (I-A) or (I-B), a first component (B), and a second component (B), wherein the second component (B) is different from the first component (B), and the weight ratio of component (A) to the sum of the first component (B) and the second component (B) is from 100:1 to 1:100, preferably from 50:1 to 1:50, more preferably from 20:1 to 1:40, even more preferably from 15:1 to 1:30, even more preferably from 12:1 to 1:25, or from 10:1 to 1:20, or from 10:1 to 1:10, or from 5:1 and 1:15, or from 5:1 to 1:5, or from 4:1 to 1:4, or from 3:1 to 1:10, or from 3:1 to 1:3, or from 2:1 to 1:5, or 1:1.

[0240] Throughout this document, the expression "composition" refers to various mixtures or combinations of the polymorph of compound (I-A) or (I-B) and component (B) (including the embodiments defined above), for example, a single "ready-mix" form, a complex spray mixture (such as a "tank mixture") composed of individual formulations of a single active ingredient component, and those in the combined use of a single active ingredient when applied sequentially, i.e., over a moderately short period such as several hours or days. The order of application of component (I-A) or (I-B) and (B) is not important in the practice of the present invention.

[0241] The above mixture can be used in a method for controlling pests, which comprises applying a composition containing the above mixture to the pests or their environment, where methods of treating the body of a human or animal by surgery or therapy, and diagnostic methods performed on the body of a human or animal are excluded.

[0242] The polymorphs according to the first or second aspect, and the mixtures containing one or more of the above active ingredients can be, for example, in a single "ready-mix" form, a composite spray mixture (such as a "tank mixture") composed of individual formulations of a single active ingredient component, and can be applied in combination with a single active ingredient when applied sequentially, i.e., over a moderately short period such as several hours or several days. The order of applying the polymorphs according to the present invention and the above active ingredients is not important in the practice of the present invention.

[0243] The composition according to the present invention may also contain, for example, stabilizers such as unepoxidized or epoxidized vegetable oils (such as epoxidized coconut oil, rapeseed oil or soybean oil), defoamers such as silicone oils, preservatives, viscosity regulators, binders and / or adhesives, fertilizers or other active ingredients for achieving specific effects, such as additional solid or liquid auxiliaries such as fungicides, fungicidal and bactericidal agents, nematicides, plant activators, molluscicides or herbicides.

[0244] The composition according to the present invention can be prepared in a manner known per se, in the absence of auxiliaries, for example, by pulverizing, screening and / or compressing the solid active ingredient, and in the presence of at least one auxiliary, for example, by homogeneously mixing and / or pulverizing the active ingredient with one or more auxiliaries. These preparation processes of the composition and the use of compound (I) for preparing these compositions are also the subject of the present invention.

[0245] Another aspect of the present invention relates to the use of a polymorph of formula (I-A) or (I-B) according to the present invention, a composition containing a polymorph of a compound of formula (I-A) or (I-B), or a fungicidal, bactericidal or pesticidal mixture containing a polymorph of a compound of formula (I-A) or (I-B) for controlling or preventing ectoparasitism on abiotic materials related to plants such as useful plants, for example, crop plants, their propagules such as seeds, harvested crops such as harvested food crops, or plant pathogenic microorganisms such as insects or preferably fungal organisms.

[0246] A further aspect of the invention relates to a method for controlling or preventing ectoparasitism of inanimate materials by phytopathogenic or putrefactive microorganisms or organisms potentially harmful to humans, such as fungal organisms, on plants, such as useful plants, including crop plants, their propagules such as seeds, or harvested crops such as harvested food crops. This method comprises applying a polymorph of a compound of formula (I-A) or (I-B) according to the invention as defined herein as an active ingredient to a plant, a part of a plant or its habitat, its propagule, or any part of the inanimate material.

[0247] Controlling or preventing means reducing ectoparasitism by insects or phytopathogenic or putrefactive microorganisms or organisms potentially harmful to humans, such as fungal organisms, to a level where improvement is demonstrated.

[0248] A preferred method for controlling or preventing ectoparasitism of crop plants by phytopathogenic microorganisms or insects, such as fungal organisms, which comprises applying a polymorph of a compound of formula (I-A) or (I-B) according to the invention or an agrochemical composition containing a polymorph of a compound of formula (I-A) or (I-B) is foliar treatment. The application frequency and application rate will depend on the risk of ectoparasitism by the corresponding pathogen or insect. However, the polymorphs according to the invention can also penetrate from the roots into the plant via the soil (osmotic translocation effect) by perfusion of the liquid formulation into the plant's habitat or by applying the compound to the soil in solid form, for example in granular form (soil application). In the case of paddy crops, such granular materials can be applied to flooded paddy fields. The polymorphs can also be applied (coated) to seeds by impregnating the seeds or tubers with a liquid formulation of a fungicide and bactericide or by coating them with a solid formulation.

[0249] For example, formulations such as compositions containing a polymorph according to the present invention and, if desired, a solid or liquid adjuvant or monomer encapsulating a polymorph of a compound of formula (I-A) or (I-B) can be prepared in a known manner, typically by homogeneously mixing the compound together with extenders such as, for example, solvents, solid carriers and any surface-active compound (surfactant) and / or by grinding.

[0250] Advantageous applications are usually from 5 g to 2 kg of active ingredient (a.i.) per hectare (ha), preferably from 10 g to 1 kg a.i. / ha, most preferably from 20 g to 600 g a.i. / ha. When used as a seed dressing, a convenient dosage is from 10 mg to 1 g of active substance per kg of seed.

[0251] When the combination according to the invention is used for the treatment of seeds, amounts of from 0.001 to 50 g of the polymorph of the compound of formula (I) per kg of seeds, preferably from 0.01 to 10 g per kg of seeds, are generally considered sufficient.

[0252] Preferably, the compositions comprising a polymorph according to the present invention are applied preventively, meaning before the onset of the disease, or therapeutically, meaning after the onset of the disease.

[0253] The composition of the present invention can be employed in any conventional form, for example, two-component systems, powders for dry seed treatment (DS), emulsions for seed treatment (ES), flowable concentrates for seed treatment (FS), solutions for seed treatment (LS), water-dispersible powders for seed treatment (WS), capsule suspensions for seed treatment (CF), gels for seed treatment (GF), emulsion concentrates (EC), suspension concentrates (SC), suspoemulsions (SE), capsule suspensions (CS), water-dispersible granules (WG), emulsifiable granules (EG), emulsions, oil-in-water type (EO), emulsions, water-in-oil type (EW), microemulsions (ME), oil dispersions (OD), oil-miscible fluids (OF), miscible oils (OL), soluble concentrates (SL), ultra-low volume suspensions (SU), ultra-low volume liquids (UL), industrial concentrates (TK), dispersible concentrates (DC), wettable powders (WP), or any technically preferred formulation in combination with an agriculturally acceptable adjuvant.

[0254] Such compositions can be produced in a conventional manner, for example, by mixing the active ingredient with a suitable inert formulation (diluent, solvent, filler, and any other formulation components such as surfactants, biocides, antifreeze agents, spreading agents, thickeners, and compounds that provide an adjuvant activity effect). Also, conventional slow-release formulations can be employed when a long-lasting efficacy is intended. In particular, formulations applied in spray forms such as water-dispersible concentrates (e.g., EC, SC, DC, OD, SE, EW, EO, etc.), wettable powders, and granules may contain surfactants such as condensates of formaldehyde and naphthalene sulfonates, alkylaryl sulfonates, lignin sulfonates, fatty alkyl sulfates, and other compounds such as ethoxylated alkylphenols and ethoxylated aliphatic alcohols that provide wetting, dispersing, and adjuvant effects.

[0255] The seed coating composition is applied to the seeds in a manner known per se, for example in a suitable seed coating composition form such as an aqueous suspension or a dry powder form having good adhesion to the seeds, using the combination and diluent of the present invention. Such seed coating compositions are known in the art. The seed coating composition may contain a single active ingredient or, for example, may contain a combination of active ingredients in encapsulated form such as sustained-release capsules or microcapsules.

[0256] Generally, the composition contains 0.01 to 90% by weight of the active agent, 0 to 20% of an agriculturally acceptable surfactant and 10 to 99.99% of a solid or liquid inert composition, and adjuvants, and the active agent is optionally composed of the polymorphs according to the present invention together with other active agents such as, in particular, microbicides, preservatives and the like. The concentrated form of the composition generally contains about 2 to 80%, preferably about 5 to 70% by weight of the active agent. The application form of the composition may contain, for example, 0.01 to 20% by weight, preferably 0.01 to 5% by weight of the active agent. Commercially available products are preferably formulated as concentrates, but end users will usually use the diluted composition.

[0257] It is preferred to formulate commercially available products as concentrates, but end users will usually dilute and use the composition.

[0258] The application rate varies within a wide range and depends on the nature of the soil, the application method, the crop plant, the pest to be controlled, the main climatic conditions, and other factors determined by the application method, the application time and the target crop. As a general guideline, the compound can be applied at a rate of 1 to 2000 l / ha, in particular 10 to 1000 l / ha.

[0259] The preferred formulation can have the following composition (% by weight): Emulsifiable concentrate: Active ingredient: 1 to 95%, preferably 60 to 90% Surfactant: 1 to 30%, preferably 5 to 20% Liquid carrier: 1 to 80%, preferably 1 to 35%

[0260] Dust: Active ingredient: 0.1 - 10%, preferably 0.1 - 5% Solid carrier: 99.9 - 90%, preferably 99.9 - 99%

[0261] Suspension concentrate: Active ingredient: 5 - 75%, preferably 10 - 50% Water: 94 - 24%, preferably 88 - 30% Surfactant: 1 - 40%, preferably 2 - 30%

[0262] Wettable powder: Active ingredient: 0.5 - 90%, preferably 1 - 80% Surfactant: 0.5 - 20%, preferably 1 - 15% Solid carrier: 5 - 95%, preferably 15 - 90%

[0263] Granules: Active ingredient: 0.1 - 30%, preferably 0.1 - 15% Solid carrier: 99.5 - 70%, preferably 97 - 85%

Brief Description of the Drawings

[0264]

Figure 1

Figure 2

Figure 3

Figure 4

Figure 5

Figure 6

Modes for Carrying Out the Invention

[0265] Abbreviations DSC Differential Scanning Calorimetry MIBK Methyl Isobutyl Ketone TFAC Trifluoroacetyl Chloride TMS Tetramethylsilane

Examples

[0266] Throughout this specification, temperature is shown in degrees Celsius (°C), and "mp." means melting point. 1 H and 19 1H NMR measurements were recorded on a Bruker 400 MHz spectrometer, and chemical shifts are reported in ppm relative to TMS( 1 1H) and CFCl3( 19 19F) standards.

[0267] Preparation Examples The following examples are for illustrative purposes of the present invention. Compounds of formula (I-A) or (I-B) can be prepared according to the above synthetic techniques.

[0268] Compounds of formula (I-A) and (I-B) were prepared according to the methods disclosed in WO 2017 / 055473, WO 2018 / 177894 and WO 2020 / 212513.

[0269] Example 1: Preparation of Polymorphs of Compound (I-A) This example shows the preparation of polymorphs of N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide (Compound (I-A))

Chemical formula

[0270] The preparation method of the compound of formula (I-A) is disclosed in WO 2018 / 177894 (Example 8b) and WO 2020 / 212513 (Example 1).

[0271] 1a) Preparation of compound (I-A) Into a 1500 mL flask, N-[[4-(N-hydroxycarbamimidoyl)phenyl]methyl]-N-methoxycyclopropanecarboxamide (93% purity, 112.9 g, 0.4 mol), MIBK (667 g) and 3,5-lutidine (145.0 g, 1.28 mol) were added. To the resulting suspension, TFAC (116.5 g, 0.88 mol) was added over 30 minutes while cooling the reaction mixture to 35 - 40 °C. After 1 hour, water (100 mL) was introduced, the contents were stirred for 10 minutes, the layers were separated, and the organic layer was washed with water (200 mL), aqueous NaHCO3 (2 × 200 g) and water (3 × 100 g). The organic layer was concentrated under reduced pressure to obtain 145 g (99% yield, 93% purity) of compound (I-A) as a yellow oil. Sometimes, the oil solidified uncontrollably during storage. 1 H NMR (400 MHz, CDCl3) δ ppm: 8.09 (d, 2H), 7.53 (d, 2H), 4.87 (s, 2H), 3.73 (s, 3H), 2.19 (m, 1H), 1.05 (m, 2H), 0.86 (m, 2H). 19 F NMR (400 MHz, CDCl3) δ ppm: -65.33 (s).

[0272] 1b) Preparation of seed crystals of the compound of formula (I-A) The oil obtained in 1a) was dissolved in methylcyclohexane, the resulting mixture was heated to 70 °C until the oil was completely dissolved, the resulting solution was slowly cooled to room temperature and held at this temperature until the crystalline form became visible. This solution was further cooled to -5 °C. The resulting crystals were filtered off and washed with methylcyclohexane to obtain compound (I-A) as a white crystalline product.

[0273] 1c) Preparation of polymorphs of compound (I-A) The oil obtained in 1a) was dissolved in methylcyclohexane, and the resulting mixture was heated to 70 °C until the oil was completely dissolved. The resulting solution was cooled to 10 °C, and seed crystals were added. After crystallization, the solution was further cooled to -5 °C and stirred for 30 minutes. The resulting crystals were filtered and washed with methylcyclohexane to obtain a white crystalline product (98.5% purity). The presence of the polymorph of the compound (I-A) of the present invention was confirmed by single crystal X-ray diffraction analysis.

[0274] Example 2: Preparation of polymorphs of compound (I-B) This example shows the preparation of polymorphs of N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide (compound I-B).

[0275] The preparation method of the compound of formula (I-B) is disclosed in International Publication No. 2018 / 177894 (Example 9b) and International Publication No. 2020 / 212513. The compound of formula (I-B):

Chemical formula

[0276] 2a) Preparation of compound (I-B) To a 250 mL reactor, N-[[4-(N-hydroxycarbamimidoyl)phenyl]methyl]-N,2-dimethoxy-propanamide (96.7% purity, 50.0 g, 0.17 mol), MIBK (200 g) and 3,5-lutidine (30.1 g, 0.28 mol) were added. The contents were stirred for 10 minutes. To this reaction mixture, 2,2,2-trifluoroacetyl chloride (TFAC) (36.4 g, 0.28 mol) was added while maintaining the temperature at 25 °C. After 2 hours, water (100 mL) was introduced, the contents were stirred for 5 minutes, the layers were separated, and the organic layer was washed with water (100 mL) and aqueous NaHCO3 (2 × 100 mL). The organic layer was concentrated under reduced pressure to obtain 61 g (94% yield, 95% purity) of compound (I-B) as an oil. Sometimes, the oil solidified uncontrollably during storage. 1 1H NMR (400 MHz, CDCl3) δ ppm: 8.09 (d, 2H), 7.48 (d, 2H), 4.98 (m, 1H), 4.80 (m, 1H), 4.27 (m, 1H), 3.71 (s, 3H), 3.34 (s, 3H), 1.37 (d, 3H). 19 19F NMR (400 MHz, CDCl3) δ ppm: -65.35 (s).

[0277] 2b) Preparation of seed crystals of the compound of formula (I-B) The oil obtained in 2a) was dissolved in methylcyclohexane, and the resulting mixture was heated to 70 °C until the oil was completely dissolved. The resulting solution was slowly cooled to room temperature and held at this temperature until the crystalline form became visible. This solution was further cooled to -5 °C. The resulting crystals were filtered off and washed with methylcyclohexane to obtain the compound (I-B) as a white crystalline product.

[0278] 2c) Preparation of polymorphs of compound (I-B) The oil was dissolved in methylcyclohexane at 70 °C. This solution was cooled to 40 °C and seed crystals were added. This solution was further cooled to -5 °C and stirred for 1 hour. The resulting crystals were filtered off and washed with methylcyclohexane to obtain a white crystalline product (56.0 g, 97.6% purity, 88% yield). The presence of the polymorph of the compound (I-B) of the present invention was confirmed by single crystal X-ray diffraction analysis.

[0279] Analysis of polymorphs After preparation by the method detailed above, the sample was subjected to analysis by powder X-ray diffraction and / or single crystal X-ray diffraction and / or differential scanning calorimetry (DSC).

[0280] Powder X-ray diffraction analysis (pXRD): Powder X-ray diffraction analysis of the solid material was performed at room temperature and relative humidity above 40% using a Bruker D8 (pXRD) powder diffractometer equipped with a Lynxeye detector. The sample was filled into an XRD holder, and the surface of the sample was flattened with a microscope slide glass. The pXRD holder was set on the instrument and rotated, and a powder pattern was collected at 2θ of 3.5° to 40° with a scanning time of 25 to 30 minutes according to the pattern intensity. The measured powder X-ray diffraction patterns of the polymorphs of compound (I-A) and compound (I-B)A are shown in Figure 1 and Figure 4, respectively.

[0281] Single crystal intensity data: Single crystal intensity data was collected using a Rigaku Corporation SuperNova diffractometer with Cu Kα radiation (λ = 1.54056 Å) and a graphite monochromator. The crystal was placed in NVH oil at 100 K to collect the data. The data was analyzed using the CRYSTALS software package. Using this data, predicted powder X-ray diffraction patterns for the polymorphs of compound (I-A) (Figure 2) and compound (I-B) were generated (Figure 5).

[0282] Differential scanning calorimetry (DSC): DSC was performed using a Mettler Toledo DSC1. A sample in an amount of about 1 to 3 mg was filled into a 40 μL aluminum sample holder and heated from 25 °C to 260 °C at a rate of 10 °C / min. A hole was made in the lid of the DSC crucible to allow the release of gas generated during heating of the sample.

[0283] The presence of the polymorphs of the present invention was confirmed by DSC analysis, and the melting points of compound (I-A) and compound (I-B) were as follows.

[0284] [Table 3]

[0285] The DSC trace of the polymorph of compound (I-A) is shown in Figure 3, and the DSC trace of the polymorph of compound (I-B)A is shown in Figure 6.

[0286] The present invention has been described with reference to preferred embodiments and examples thereof, but the scope of the present invention is not limited only to the described embodiments. As will be apparent to those skilled in the art, it is possible to make modifications and adaptations to the above invention without departing from the spirit and scope of the present invention, which are defined and limited by the appended claims. All publications cited herein are hereby incorporated by reference in their entirety for all purposes to the same extent as if each individual publication was specifically and individually indicated to be incorporated by reference.

Claims

1. A crystalline polymorph of a compound of formula I-A 【Chemical 1】 having an X-ray diffraction pattern comprising four or more 2θ angle values selected from the group consisting of 11.9 ± 0.2, 12.5 ± 0.2, 16.5 ± 0.2, 17.1 ± 0.2, 19.5 ± 0.2, 22.1 ± 0.2, 23.9 ± 0.2 and 24.9 ± 0.

2.

2. A crystalline polymorph of a compound of formula I-B 【Chemical 2】 having an X-ray diffraction pattern comprising four or more 2θ angle values selected from the group consisting of 8.7 ± 0.2, 9.7 ± 0.2, 14.4 ± 0.2, 15.8 ± 0.2, 17.3 ± 0.2 and 20.7 ± 0.

2.

3. The following lattice parameters: a = 15.2 ± 0.1 Å, b = 4.8 ± 0.1 Å, c = 21.5 ± 0.1 Å, α = 90 ± 0.2°, β = 106.4 ± 0.2°, γ = 90 ± 0.2°, and a volume of 1508 ± 16 Å 3 The crystalline polymorph of formula (I-A) according to claim 1, having the above

4. The crystalline polymorph of formula (I-A) according to claim 1 or claim 3, having a melting point of 38.6 °C.

5. The following lattice parameters: a = 7.4 ± 0.1 Å, b = 18.2 ± 0.1 Å, c = 12.7 ± 0.1 Å, α = 90 ± 0.2°, β = 104.3 ± 0.2°, γ = 90 ± 0.2°, and a volume of 1664 ± 17 Å 3 The crystalline polymorph of formula (I-B) according to claim 2, having the same

6. The crystalline polymorph of formula (I-B) according to claim 2 or claim 5, having a melting point of 63.5 °C.

7. An agricultural composition comprising a polymorph of formula (I-A) or a polymorph of formula (I-B) according to any one of claims 1 to 6, and at least one agriculturally acceptable carrier or diluent.

8. A method for controlling or preventing ectoparasitism on useful plants caused by phytopathogenic microorganisms, comprising applying, as an active ingredient, a fungicidal and antifungal effective amount of a polymorph of formula (I-A) or a polymorph of formula (I-B) according to any one of claims 1 to 6, or a composition comprising said polymorph, to said plant, a part thereof or its habitat.

9. The method according to claim 8, wherein the compound is a compound of formula I-A [Chemical Formula 3]

10. The method according to claim 8, wherein the compound is a compound of formula I-B

11. 【Chemical Formula 4】 The method according to claim 8 or 9, wherein the plant is a genetically modified plant selected from soybeans.

12. The method according to any one of claims 8 to 11, wherein the plant is a Bt soybean plant.

13. Use of a polymorph of formula (I-A) or a polymorph of formula (I-B) according to any one of claims 1 to 6 as a fungicide and antifungal agent.

14. Use of a polymorph of formula (I-A) or a polymorph of formula (I-B) according to any one of claims 1 to 6 for controlling Phakopsora pachyrhizi in genetically modified soybean plants.

15. The use according to claim 14, wherein the genetically modified soybean plant is a Bt soybean plant. ​ ​

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