Polymorphs of methoxy cinnamate derivatives

Abstract

The present invention relates to crystalline forms of the compound (Z)-2-(5-cyclohexyl-2-methyl-5-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester, compositions comprising said crystalline forms and methods of use thereof as fungicides.

Description

[0001] This invention relates to the solid forms of substituted methoxyacrylate derivatives, compositions comprising these solid forms, and methods of using them as fungicides.

[0002] WO 2020 / 193387, WO 2021 / 176057 and WO 2022 / 200579 describe the use of methoxyacrylate derivatives for combating plant pathogenic fungi and methods for preparing said methoxyacrylate derivatives, particularly methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate shown below.

[0003]

[0004] New solid forms of this compound, their compositions, and methods for their preparation and use have now been discovered.

[0005] According to one embodiment of the invention, a novel crystalline polymorph form of compound (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester is provided, designated as 'Form A'.

[0006] In a first aspect of the invention, a crystalline polymorph form A of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate is provided, wherein the polymorph has an X-ray diffraction pattern containing peaks at 12.0° ± 0.2°, 18.6° ± 0.2°, 20.3° ± 0.2° and 22.0° ± 0.2° 2θ, as measured by X-ray diffraction using an X-ray wavelength of 1.5406 Å.

[0007] In another embodiment, a novel crystalline polymorph form of compound (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester is provided, designated as 'Form B'.

[0008] According to a second aspect of the invention, a crystalline polymorph form B of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate is provided, wherein the polymorph has an X-ray diffraction pattern containing peaks at 12.2° ± 0.2°, 18.7° ± 0.2°, 20.4° ± 0.2° and 24.4° ± 0.2° 2θ, as measured by X-ray diffraction using an X-ray wavelength of 1.5406 Å.

[0009] In another embodiment, a novel crystalline polymorph form of compound (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester is provided, designated as 'Form C'.

[0010] According to a third aspect of the invention, a crystalline polymorph form C of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate is provided, wherein the polymorph has an X-ray diffraction pattern containing peaks at 12.1° ± 0.2°, 19.5° ± 0.2°, 20.7° ± 0.2° and 22.3° ± 0.2° 2θ, as measured by X-ray diffraction using an X-ray wavelength of 1.54184 Å.

[0011] According to a fourth aspect of the invention, an agricultural chemical composition is provided comprising a crystalline polymorph of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate in form A, or form B, or form C, and an agriculturally chemically acceptable carrier or diluent.

[0012] According to a fifth aspect of the invention, a method for controlling or preventing infection in plants caused by plant pathogenic fungi is provided, wherein a fungicide-effective amount of a crystalline polymorph of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate in form A, or form B, or form C, or a composition comprising said polymorph as an active ingredient, is applied to the plants, parts thereof, or the site thereof.

[0013] According to a sixth aspect of the invention, a method for controlling or preventing infection in plants caused by plant pathogenic fungi is provided, wherein the plant pathogenic fungi contain an F129L mutation in mitochondrial cytochrome b conferring resistance to QoI inhibitors, the method comprising applying a polymorph as described herein, or a composition comprising the polymorph as an active ingredient, to the plant, a portion thereof, or a site thereof.

[0014] The crystalline polymorph designated as Form A of the present invention can be characterized by the unit cell parameters of its single crystal as shown in Table 1 below. This polymorph was obtained using the method described in Example 1.

[0015] Table 1

[0016]

[0017] In this table, a, b, c = the length of the edge of the unit cell, and α, β, γ = the angle of the unit cell.

[0018] Therefore, in one embodiment of the invention, the crystalline polymorph (form A) of the invention has the following lattice parameters: a = 12.7 Å ± 0.1, b = 11.0 Å ± 0.1, c = 13.1 Å ± 0.1, α = 90.0° ± 0.2°, β = 110.2° ± 0.2°, γ = 90.0° ± 0.2° and volume = 1706.6 Å. 3 ± 17 Å 3 .

[0019] The crystalline polymorph (form A) can also be characterized by powder X-ray diffraction patterns expressed in 2θ angles or d-intervals. Therefore, in another embodiment of the invention, the crystalline polymorph (form A) of the invention has a powder X-ray diffraction pattern containing peaks at 12.0° ± 0.2°, 18.6° ± 0.2°, 20.3° ± 0.2°, and 22.0° ± 0.2° 2θ, as measured by X-ray diffraction using an X-ray wavelength of 1.5406 Å (Cu Kα). Preferably, the polymorph further exhibits peaks at 16.5° ± 0.2°, 18.2° ± 0.2°, 23.5° ± 0.2°, 24.7° ± 0.2°, and 26.6° ± 0.2° 2θ. More preferably, the polymorph further exhibits peaks at 14.9° ± 0.2°, 16.9° ± 0.2°, 17.7° ± 0.2°, 21.5° ± 0.2°, 21.8° ± 0.2°, 24.5° ± 0.2° and 27.4° ± 0.2° 2θ.

[0020] In a preferred embodiment of the invention, the crystalline polymorph (form A) of the invention has a powder X-ray diffraction pattern containing peaks at 2θ at 12.0° ± 0.2°, 16.5° ± 0.2°, 18.2° ± 0.2°, 18.6° ± 0.2°, 20.3° ± 0.2°, 22.0° ± 0.2°, 23.5° ± 0.2°, 24.7° ± 0.2° and 26.6° ± 0.2°, as measured by X-ray diffraction using an X-ray wavelength of 1.5406 Å.

[0021] In another preferred embodiment of the invention, the crystalline polymorph (form A) of the invention has a powder X-ray diffraction pattern containing peaks at 2θ at 12.0° ± 0.2°, 14.9° ± 0.2°, 16.5° ± 0.2°, 16.9° ± 0.2°, 17.7° ± 0.2°, 18.2° ± 0.2°, 18.6° ± 0.2°, 20.3° ± 0.2°, 21.5° ± 0.2°, 21.8° ± 0.2°, 22.0° ± 0.2°, 23.5° ± 0.2°, 24.5° ± 0.2°, 24.7° ± 0.2°, 26.6° ± 0.2°, and 27.4° ± 0.2°, as measured by X-ray diffraction using an X-ray wavelength of 1.5406 Å.

[0022] In another preferred embodiment of the invention, the crystalline polymorph (form A) of the invention has a composition substantially as follows Figure 1 Powder X-ray diffraction patterns of the peaks shown in the image and listed in Table 2 below (along with the corresponding d-spacing and relative intensity values):

[0023] Table 2 - Formation of compound (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester PXRD Peak Listing Table for Formula A

[0024]

[0025] In another embodiment of the invention, a crystalline polymorph (form A) of methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxy-prop-2-enoate is provided, wherein the polymorph has a melting point of 101°C to 107°C (preferably 101°C to 106°C, more preferably 102°C to 106°C, and even more preferably 102°C to 105°C). This melting point was obtained using differential scanning calorimetry (DSC) at a heating rate of 10°C / min.

[0026] The other crystalline polymorphs designated as Form B of the present invention can be obtained using the method described in Example 2.

[0027] The crystalline polymorph (form B) can also be characterized by powder X-ray diffraction patterns expressed in terms of 2θ angles or d-intervals. Therefore, in another embodiment of the invention, a crystalline polymorph form B of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate is provided, wherein the polymorph has an X-ray diffraction pattern containing peaks at 2θ at 12.2° ± 0.2°, 18.7° ± 0.2°, 20.4° ± 0.2°, and 24.4° ± 0.2°, as measured by X-ray diffraction using an X-ray wavelength of 1.5406 Å. Preferably, the polymorph further exhibits peaks at 8.4° ± 0.2°, 10.2° ± 0.2°, 18.5° ± 0.2°, 22.1° ± 0.2°, 22.9° ± 0.2°, 23.7° ± 0.2°, and 24.9° ± 0.2° 2θ. More preferably, the polymorph further exhibits peaks at 15.9° ± 0.2°, 17.4° ± 0.2°, 18.2° ± 0.2°, 23.3° ± 0.2°, and 27.6° ± 0.2° 2θ.

[0028] In a preferred embodiment of the invention, the crystalline polymorph (form B) of the invention has a powder X-ray diffraction pattern containing peaks at 2θ at 8.4° ± 0.2°, 10.2° ± 0.2°, 12.2° ± 0.2°, 18.5° ± 0.2°, 18.7° ± 0.2°, 20.4° ± 0.2°, 22.1° ± 0.2°, 22.9° ± 0.2°, 23.7° ± 0.2°, 24.4° ± 0.2°, and 24.9° ± 0.2°, as measured by X-ray diffraction using an X-ray wavelength of 1.5406 Å.

[0029] In another preferred embodiment of the invention, the crystalline polymorph (form B) of the invention has a powder X-ray diffraction pattern containing peaks at 2θ at 8.4° ± 0.2°, 10.2° ± 0.2°, 12.2° ± 0.2°, 15.9° ± 0.2°, 17.4° ± 0.2°, 18.2° ± 0.2°, 18.5° ± 0.2°, 18.7° ± 0.2°, 20.4° ± 0.2°, 22.1° ± 0.2°, 22.9° ± 0.2°, 23.3° ± 0.2°, 23.7° ± 0.2°, 24.4° ± 0.2°, 24.9° ± 0.2° and 27.6° ± 0.2°, as measured by X-ray diffraction using an X-ray wavelength of 1.5406 Å.

[0030] In another preferred embodiment of the invention, the crystalline polymorph (form B) of the invention has a composition substantially as follows Figure 2 Powder X-ray diffraction patterns of the peaks shown in the image and listed in Table 3 below (along with the corresponding d-spacing and relative intensity values):

[0031] Table 3 - Formation of compound (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester PXRD Peak Listing Table for Formula B

[0032]

[0033] In another embodiment of the invention, a crystalline polymorph (form B) of compound (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester is provided, wherein the polymorph has a melting point of 94°C to 98°C (preferably 95°C to 97°C). This melting point was obtained using differential scanning calorimetry (DSC) at a heating rate of 10°C / min.

[0034] The other crystalline polymorphs specified as form C of the present invention can be obtained using the method described in Example 3.

[0035] The crystalline polymorph (form C) can also be characterized by powder X-ray diffraction patterns expressed in terms of 2θ angles or d-intervals. Therefore, in another embodiment of the invention, a crystalline polymorph form C of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate is provided, wherein the polymorph has an X-ray diffraction pattern containing peaks at 2θ at 12.1° ± 0.2°, 19.5° ± 0.2°, 20.7° ± 0.2°, and 22.3° ± 0.2°, as measured by X-ray diffraction using an X-ray wavelength of 1.54184 Å. Preferably, the polymorph further exhibits peaks at 8.9° ± 0.2°, 16.4° ± 0.2°, 17.6° ± 0.2°, 18.1° ± 0.2°, 21.4° ± 0.2°, 24.9° ± 0.2°, and 25.0° ± 0.2° 2θ. More preferably, the polymorph further exhibits peaks at 15.7° ± 0.2°, 24.3° ± 0.2°, 26.5° ± 0.2°, 27.6° ± 0.2°, 28.1° ± 0.2° 2θ, and 28.6° ± 0.2° 2θ.

[0036] In a preferred embodiment of the invention, the crystalline polymorph (form C) of the invention has a powder X-ray diffraction pattern containing peaks at 8.9° ± 0.2°, 12.1° ± 0.2°, 16.4° ± 0.2°, 17.6° ± 0.2°, 18.1° ± 0.2°, 19.5° ± 0.2°, 20.7° ± 0.2°, 21.4° ± 0.2°, 22.3° ± 0.2° 2θ, 24.9° ± 0.2°, and 25.0° ± 0.2° 2θ, as measured by X-ray diffraction using an X-ray wavelength of 1.54184 Å.

[0037] In another preferred embodiment of the invention, the crystalline polymorph (form C) of the invention has 2θ values ​​comprising 8.9° ± 0.2°, 12.1° ± 0.2°, 15.7° ± 0.2°, 16.4° ± 0.2°, 17.6° ± 0.2°, 18.1° ± 0.2°, 19.5° ± 0.2°, 20.7° ± 0.2°, 21.4° ± 0.2°, 22.3° ± 0.2° 2θ, 24.3° ± 0.2°, 24.9° ± 0.2°, 25.0° ± 0.2°, 26.5° ± 0.2°, 27.6° ± 0.2°, 28.1° ± 0.2° 2θ, and 28.6° ± 0.2°. The powder X-ray diffraction pattern of the peak at 2θ, as measured by X-ray diffraction using an X-ray wavelength of 1.54184 Å.

[0038] In another preferred embodiment of the invention, the crystalline polymorph (form C) of the invention has a composition substantially as follows Figure 3 Powder X-ray diffraction patterns of the peaks shown in the image and listed in Table 4 below (along with the corresponding d-spacing and relative intensity values):

[0039] Table 4 - Formation of compound (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester List of peaks in PXRD prediction plot for formula C

[0040]

[0041] The crystalline polymorph designated as Form C of the present invention can also be characterized by the unit cell parameters of its single crystal, as shown in Table 5 below. This polymorph was obtained using the method described in Example 1.

[0042] Table 5

[0043]

[0044] In this table, a, b, c = the length of the edge of the unit cell, and α, β, γ = the angle of the unit cell.

[0045] Therefore, in one embodiment of the invention, the crystalline polymorph (form C) of the invention has the following lattice parameters: a = 11.8 Å ± 0.1, b = 11.3 Å ± 0.1, c = 12.8 Å ± 0.1, α = 90.0° ± 0.2°, β = 107.5° ± 0.2°, γ = 90.0° ± 0.2° and volume = 1631.1 Å. 3 ± 16 Å 3 . Attached Figure Description

[0046] Figure 6 - The predicted ideal solubility of polymorphs A and B of the present invention, using melting point and heat of fusion data of different polymorphs and the nonlinear Van't Hoff equation as reported in the International Journal of Pharmaceutics, 18 (1984) 25-38, is shown (as a solubility-to-temperature curve). It is also well known that the Van't Hoff equation can be used to determine the thermodynamic stability of different polymorphs; see Crystal Growth & Design, Vol. 3, No. 6, 2003. Therefore, the predicted ideal solubility can be calculated as follows:

[0047] x = exp(-ΔHf / R (1 / T - 1 / Tm))

[0048] in

[0049] x: Soluble mole fraction

[0050] exp: Exponential function

[0051] ΔHf: Heat of fusion (J / mol) (obtained from DSC data)

[0052] R: gas constant (8.314 J / mol·K)

[0053] T: Target temperature (K)

[0054] Tm: Melting point (K) (obtained from DSC data)

[0055] When using the disclosed thermal data obtained for the claimed polymorphic forms A and B, from the solubility-temperature comparison plot ( Figure 6As can be seen, compared to form B, form A is a polymorph that is stable under single-phase transformation. For agricultural chemical products, to avoid failure caused by polymorphic transformation, a form with lower solubility and greater thermodynamic stability is desirable; in this case, form A is preferred.

[0056] In the context of this invention, a polymorph is a specific crystalline form of a compound that can exist in more than one crystalline form in the solid state. A crystalline form of a compound contains constituent molecules arranged in an ordered repeating pattern (extending in all three spatial dimensions) (in contrast, amorphous solid forms lack long-range order in molecular positions). Different polymorphs of a compound have different atomic and / or molecular arrangements in their crystal structures. When the compound is a bioactive compound (such as a fungicide), differences in crystal structure can lead to different polymorphs with different chemical, physical, and biological properties. Properties that may be affected include crystal shape, density, hardness, color, chemical stability, melting point, water absorption, suspension rate, dissolution rate, and bioavailability. Therefore, a specific polymorph can possess properties that make it more advantageous than another polymorph of the same compound for a particular use: in particular, the physical, chemical, and biological properties listed above have a significant impact on manufacturing methods and formulation development, the ease with which the compound can be combined with other active ingredients and formulation components in formulations, and the quality and efficacy of plant treatments (such as fungicides). It should be pointed out that it is impossible to predict whether a compound can exist in a solid state as more than one polymorph, nor is it possible to predict the properties of any of these polymorphs.

[0057] In particular, using a specific polymorph allows for the use of novel formulations compared to the presence of a compound in a polycrystalline / amorphous form. This can be advantageous for many reasons. For example, suspension concentrate (SC) formulations may be preferred over emulsion concentrate (EC) formulations because the lack of solvent in SCs generally means that the formulation may have lower phytotoxicity than an equivalent EC formulation—however, if the form in which the compound is present is unstable in such an SC formulation, polymorphic transformation may occur, leading to undesirable crystal growth. This crystal growth is detrimental because it results in, for example, thickening and potential solidification of the formulation, which can cause clogging of application equipment, such as spray nozzles in agricultural application machinery. Using a stable polycrystalline form will overcome these problems.

[0058] The presence of crystals in a solid phase can be determined using conventional methods known in the art. For example, powder X-ray diffraction is a convenient and routine method. Other techniques that can be used include differential scanning calorimetry (DSC), thermogravimetric analysis (TGA), and Raman or infrared spectroscopy, NMR, gas chromatography, or HPLC. Single-crystal X-ray diffraction is particularly useful for identifying crystal structures.

[0059] The polymorph of the present invention can be applied in its unchanged form, but is more preferably incorporated into agricultural chemical compositions by conventional means. Therefore, in another aspect, the present invention provides an agricultural chemical composition comprising the polymorph of the present invention as defined above and at least one agriculturally acceptable carrier or diluent.

[0060] In one embodiment, an agrochemical composition is provided comprising a crystalline polymorph (Form A) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein and an agrochemically acceptable carrier or diluent.

[0061] In another embodiment, an agricultural chemical composition is provided comprising a crystalline polymorph (form B) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein and an agriculturally chemically acceptable carrier or diluent.

[0062] In another embodiment, an agricultural chemical composition is provided comprising a crystalline polymorph (form C) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein and an agriculturally chemically acceptable carrier or diluent.

[0063] In another embodiment of the invention, a method for controlling or preventing infection in plants caused by plant pathogenic fungi is provided, wherein a fungicide-effective amount of a crystalline polymorph (form A) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate, as defined herein, or a composition comprising said polymorph as an active ingredient, is applied to the plants, parts thereof, or the site thereof.

[0064] In another embodiment of the invention, a method for controlling or preventing infection in plants caused by plant pathogenic fungi is provided, wherein a fungicide-effective amount of a crystalline polymorph (form B) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate, as defined herein, or a composition comprising said polymorph as an active ingredient, is applied to the plants, parts thereof, or the site thereof.

[0065] In another embodiment of the invention, a method for controlling or preventing infection in plants caused by plant pathogenic fungi is provided, wherein a fungicide-effective amount of a crystalline polymorph (form C) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate, as defined herein, or a composition comprising said polymorph as an active ingredient, is applied to the plants, parts thereof, or the site thereof.

[0066] In one embodiment of the invention, a method is provided for controlling or preventing infection in plants caused by plant pathogenic fungi, wherein the plant pathogenic fungi contain an F129L mutation in mitochondrial cytochrome b conferring resistance to QoI inhibitors, the method comprising applying a fungicide-effective amount of a crystalline polymorph (form A) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate, as defined herein, or a composition comprising said polymorph as an active ingredient, to the plant, its parts, or the site thereof.

[0067] In another embodiment of the invention, a method is provided for controlling or preventing infection in plants caused by plant pathogenic fungi, wherein the plant pathogenic fungi contain an F129L mutation in mitochondrial cytochrome b conferring resistance to QoI inhibitors, the method comprising applying a fungicide-effective amount of a crystalline polymorph (form B) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate, as defined herein, or a composition comprising said polymorph as an active ingredient, to the plant, its parts, or the site thereof.

[0068] In another embodiment of the invention, a method is provided for controlling or preventing infection in plants caused by plant pathogenic fungi, wherein the plant pathogenic fungi contain an F129L mutation in mitochondrial cytochrome b conferring resistance to QoI inhibitors, the method comprising applying a fungicide-effective amount of a crystalline polymorph (form C) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate, as defined herein, or a composition comprising said polymorph as an active ingredient, to the plant, its parts, or the site thereof.

[0069] If appropriate, polymorphs of compound (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxy-prop-2-enoic acid methyl ester (form A, or form B, or form C) and, where appropriate, its tautomers (in each case, in free or salt form) can also be obtained as hydrates and / or contain other solvents, such as those that can be used to crystallize compounds present in solid form.

[0070] For practical purposes, the polymorphs (form A, or form B, or form C) of compound (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester have a very favorable level of bioactivity for protecting plants from fungal diseases.

[0071] The polymorphs (form A, or form B, or form C) of the compound (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-propane-2-enoate according to the present invention can be used in the agricultural sector and related application fields as active ingredients, for example, for controlling plant pests, or for controlling putrefactive microorganisms or potentially harmful organisms on non-living materials. These novel polymorphs are characterized by excellent activity at low application rates, good plant tolerance, and environmental safety. They possess highly useful therapeutic, preventative, and systemic properties and can be used to protect a variety of cultivated plants. The polymorphs (form A, or form B, or form C) of the compound (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-propane-2-enoate can be used to inhibit or destroy pests appearing on plants or plant parts (fruits, flowers, leaves, stems, tubers, roots) of various useful plant crops, while also protecting those plant parts that grow later from, for example, plant pathogenic microorganisms.

[0072] The present invention further relates to a method for controlling or preventing infection of microbially susceptible plants or plant propagation material and / or harvested food crops by treating plants or plant propagation material and / or harvested food crops, wherein a fungicide-effective amount of a crystalline polymorph (form A, or form B, or form C) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate is applied to these plants, their parts or sites.

[0073] In one embodiment, the present invention relates to a method for controlling or preventing infection of microbially susceptible plants or plant propagation material and / or harvested food crops by treating plants or plant propagation material and / or harvested food crops, wherein a fungicide-effective amount of a crystalline polymorph (form A) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate, as defined herein, is applied to these plants, parts thereof, or the site thereof.

[0074] In another embodiment, the present invention relates to a method for controlling or preventing infection of microbially susceptible plants or plant propagation material and / or harvested food crops by treating plants or plant propagation material and / or harvested food crops, wherein a fungicide-effective amount of a crystalline polymorph (form B) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate, as defined herein, is applied to these plants, parts thereof, or the site thereof.

[0075] In another embodiment, the present invention relates to a method for controlling or preventing infection of microbially susceptible plants or plant propagation material and / or harvested food crops by treating plants or plant propagation material and / or harvested food crops, wherein a fungicide-effective amount of a crystalline polymorph (form C) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate, as defined herein, is applied to these plants, parts thereof, or the site thereof.

[0076] As used herein, the term "fungicide" means a compound that controls, alters, or prevents the growth of fungi. The term "effective fungicide amount" means the amount of such a compound or combination of such compounds that can affect fungal growth. Controlling or altering effects include all deviations from natural development, such as killing, inhibiting, etc., and prevention includes the formation of barriers or other defenses within or on the plant to prevent fungal infection.

[0077] The term "plant" refers to all the tangible parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, culms, leaves, and fruits.

[0078] The term "plant propagation material" refers to all reproductive parts of a plant, such as seeds or vegetative parts like cuttings and tubers. It includes seeds in the strict sense, as well as roots, fruits, tubers, bulbs, rhizomes, and other parts of the plant.

[0079] As used herein, the term "site" means the place in which or on which a plant grows, or the place where the seeds of a cultivated plant are sown, or the place where the seeds will be placed in the soil. It includes soil, seeds, seedlings, and established vegetation.

[0080] In addition, polymorphs (form A, or form B, or form C) of the compound (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester as defined herein can be used to control fungi in related fields, such as for the protection of industrial materials (including wood and wood-related industrial products), food storage, and hygiene management.

[0081] In addition, the present invention can also be used to protect non-living materials (e.g., wood, wall panels, and coatings) from fungal invasion.

[0082] Polymorphs (form A, or form B, or form C) of the compound (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester as defined herein are effective against fungal vectors and plant pathogenic bacteria and viruses, for example.

[0083] Polymorphs of (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxy-prop-2-enoic acid methyl ester (form A, or form B, or form C) as defined herein and / or agricultural chemical compositions containing polymorphs of the present invention effectively control broad-spectrum plant diseases, such as leaf and / or soil-borne pathogens of ornamental plants, turf, vegetables, fields, cereals, and fruit crops.

[0084] These pathogens may include:

[0085] The class Oomycetes includes species of the genus *Phytophthora*, such as *Phytophthora cactorum*, *Phytophthora capsici*, *Phytophthora cinnamomi*, *Phytophthora citricola*, *Phytophthora citrophthora*, *Phytophthora erythroseptica*, *Phytophthora fragariae*, *Phytophthora infestans*, *Phytophthora nicotianae*, *Phytophthora porri*, and *Phytophthora sojae*; and species of the genus *Pythium*, such as *Pythium aphanidermatum* and *Pythium spp.* *Pythium arrhenomanes*, *Pythium graminicola*, *Pythium irregulare*, and *Pythium ultimum*; other perennial fungi, such as *Bremia lactucae*, *Hyaloperonospora parasitica*, *Hyaloperonospora brassicae*, *Sclerophthoramacrospora*, and *Sclerospora graminicola*; species of the genus *Peronospora*, including *Peronospora destructor*, *Peronospora farinosa* f. sp. *spinaciae*, and *Peronospora viciae* f. sp.*Plasmopara* species, including *Plasmopara halstedii* and *Plasmopara viticola*; *Pseudoperonospora* species, including *Pseudoperonospora cubensis* and *Pseudoperonospora humili*; *Peronosclerospora* species, including *Peronosclerospora maydis*, *Peronosclerospora philippinensis*, and *Peronosclerospora sorghi*; and *Albugo candida* and *Albugo sorghi*. *Occidentalis*, and *Albugotragopogonis*; and *Saprolegnia*, such as species of the genus *Aphanomyces*, including *Aphanomyces cochliodes*.

[0086] The class Ascomycota includes the order Coccidioides, such as *Actinothyrium graminis* and *Asperisporium caricae*, and species of the genus *Cercospora*, including *Cercospora arachidicola*, *Cercospora beticola*, *Cercospora brassicicola*, *Cercospora canescens*, *Cercospora cf. flagellaris*, *Cercospora janseana*, *Cercospora kikuchii*, *Cercospora lagenariae*, *Cercospora sojinae*, *Cercospora sorghi*, and *Cercospora maize*. zeae-maydis); Dothistroma septosporum, Fulvia fulva, species of the genus Mycosphaerella, including Mycosphaerella pomi and Mycosphaerella linicola; Neopseudocercosporella brassicae, Neopseudocercosporella capsellae, Nothopassalora personata, Nothophaeocrytopus gaeumannii, Passalora bataticola, Passalora koepkei, Pseudocercospora griseola, Pseudocercospora banana *Pseudocercospora musaei*, *Pseudocercospora vitis*, *Pseudocercospora fijiensis*, and species of the genus *Ramularia*, including *Ramularia beticola* and *Ramularia collo-cygni*.*Ramulariopsis gossypii*, *Ramulariopsis pseudodoglycines*, *Ramulispora sorghi*, *Scolecostigminapalmivora*, *Septoria* species including *Septoria apiicola*, *Septoria glycines*, and *Septoria lycopersici*; *Zasmidium citri-griseum* and *Zymosepotria tritici*; *Helotiales*, such as *Blumeriella jaapii*, *Botrytis* species including *Botrytis cinerea* and *Botrytis spp.* *Botrytis aclada* and *Botrytis fabae*; *Botryotinia squamosa*, *Cadophora gregata*, *Civorinia allii*, *Claireedia homoeocarpa*, *Diplocarpon coronariae*, *Diplocarpon rosae*, *Drepanopeziza campestris*, *Gloeotinia temulenta*, *Hymenoscyphus fraxineus*, *Leptotrochila medicaginis*, *Marssonina graminicola*, and species of the genus *Monilinia*, including *Monilinia fructicola*, *Monilinia fructigena*, and *Monilinia laxa*.The pathogens causing perennial apple bull's eye rot include *Neofabraea perennans*, *Neofabraea vagabunda*, *Oculimacula yallundae*, species of *Pezicula*, *Pseudopeziza medicaginis*, *Pseudopeziza tracheiphila*, and species of *Pyrenopeziza*, including *Pyrenopeziza brassicae*. Other pathogens include *Rhabdoclinepseudotsugae*, species of *Rhynchosporium*, including *Rhynchosporium secalis*, and species of *Sclerotinia*, including *Sclerotinia minor*, *Sclerotinia borealis*, and *Sclerotinia*. Sclerotiorum; Hypocreales, such as *Acremonium strictum*, *Albifimbria verrucaria*, *Claviceps africana*, *Claviceps purpurea*, and species of the genus *Fusarium*, including *Fusarium avenaceum*, *Fusarium culmorum*, *Fusarium fjikuroi*, *Fusarium graminearum*, *Fusarium incarnatum*, *Fusarium langsethiae*, *Fusarium moniliforme*, *Fusarium oxysporum*, *Fusarium oxysporum f.sp. cubense*, *Fusarium poae*, and *Fusarium* var. *cubense*. The species are *Fusarium proliferatum*, *Fusarium seudograminearum*, *Fusarium subglutinans*, *Fusarium sulphureum*, *Fusarium tricinctum*, and *Fusarium verticillioides*.Species of the genus *Gliocladium*, *Neocosmospora phaseoli*, *Neocosmospora solani*, *Neonectria candida*, *Paramyrothecium roridum*, and *Sarocladium oryzae*; species of the genus *Trichoderma*, including *Trichoderma harzianum*, *Trichodermapseudokoningii*, and *Trichoderma viride*; *Trichothecium roseum* and *Ustilaginoidea virens*; and species of the order *Gaeumannomyces*, such as *Gaeumannomyces avenae*, *Gaeumannomyces graminis*, and *Gaeumannomyces graminis*. *Tritici*, *Gaeumannomyces wongoonoo*, *Magnaporthiopsis poae*, species of *Pyricularia* including *Pyricularia grisea* and *Pyricularia oryzae*; *Alternaria* species, including *Alternaria allii*, *Alternaria alternata*, *Alternaria arachidis*, *Alternaria brassicae*, *Alternaria brassicicola*, *Alternaria citri*, *Alternaria dauci*, *Alternaria grandisi*, *Alternaria helianthicola*, and *Alternaria*. Alternaria linariae, Alternaria mali, Alternaria porri, Alternaria solani, and Alternaria tomato.The fungus *Boeremia coffeae*, belonging to the genus *Ascochyta*, including *Ascochyta pisi* and *Ascochytarabiei*; species of *Bipolaris maydis*, *Bipolaris oryzae*, *Bipolaris sorokiniana*, *Cochliobolus*, *Corynespora cassiicola*, and *Curvularia*, including *Curvularia australisiensis*, *Curvularia cactivora*, and *Curvularia lunata*; and species of the genus *Didymella*, including *Didymella pinodella* and *Didymela*. pinodes); Xenodidymella applanata, species of the genus Drechslera, including Drechslera glycines; Epicoccumnigrum, Exserohilum turcicum, species of the genus Helminthosporium, including Helminthosporium solani;*Hendersonia creberrima*, *Leptosphaerulina crassiasca*, *Neocamarosporium betae*, *Ophiosphaerella agrostidis*, *Ophiosphaerella herpotricha*, *Ophiosphaerella korrae*, *Ophiosphaerella narmari*, *Parastagonospora nodorum*, *Phaeosphaeria herpotrichoides*, *Phaerosphaeria maydis*, species of the genus *Phoma*, *Plenodomus lindquistii* (sunflower black stem causal agent), *Plenodomus lingam* (cruciferous vegetable black stem causal agent), species of the genus *Pseudopyrenochaeta*, and *Pseudopyrenochaeta* (tomato pseudoechinocastroses). *Pyrenophora* species, including *Pyrenophora poae*, *Pyrenophorateres*, and *Pyrenophora tritici-repentis*; *Remotididymella destructiva*, *Stagonospora tainanensis*, and *Stagonosporopsis cucurbitacearum*; *Stemphylium* species, including *Stemphylium botryosum*, *Stemphylium solani*, and *Stemphylium vesicarium*; and *Anisogramma anonmala*, *Apiognomonia errabunda*, and *Cytospora*. platani), species of the genus Diaporthe, including Diaporthe amygdali, Diaporthehelianthin, Diaporthe neoviticola, and Diaporthephaseolorum.Species of the genus *Dicarpella*, *Discula destructiva*, *Gnomoniopsis fructicola*, *Greeneria uvicola*, *Juglanconis juglandina*, *Ophiognomonia clavigignenti-juglandacearum*, *Stenocarpella maydis*, and *Tubakia dryina*; species of the order *Dicarpella*, such as those of the genus *Aureobasidium*, including *Aureobasidium pullulans*; *Discosphaerina fulvida*; species of the order *Powdery mildew*, such as *Blumeria graminis* and *Brasiliomyces malachrae*; and species of the genus *Erysiphe*, including *Erysiphe beetula*. betae, Erysiphe crucifera powdery mildew (Erysiphe cruciferaarum), Erysiphe diffusa, Erysiphe heraclei, Erysiphe necator, and Erysiphe pisi.Powdery mildew fungi of the Asteraceae family include *Golovinomyces cichoracearum*, *Golovinomyces orontii*, *Leveillula taurica*, *Oidium arachidisi*, *Oidium neolycoperisci*, and *Phyllactinia guttata*. Species in the genus *Podosphaera* include *Pososphaera aphanis*, *Podosphaera fuliginea*, *Podosphaera fusca*, *Podosphaera leucotricha*, *Podosphaera macularis*, *Podosphaera morsuvae*, *Podosphaera pannosa*, and *Podosphaera trifida*. *Tridactyla* and *Podosphaera xanthii*; *Colletotrichum* order, such as species of the genus *Colletotrichum*, including *Colletotrichum acutatum*, *Colletotrichum cereale*, *Colletotrichum chrysanthemi*, *Colletotrichum cliviicola*, *Colletotrichum coccodes*, *Colletotrichum fragariae*, *Colletotrichum gloeosporioides*, *Colletotrichum graminicola*, *Colletotrichum lentis*, *Colletotrichum lindemuthianum*, *Colletotrichum musae*, and *Colletotrichum cucurbita*. orbiculare, Colletotrichum siamense, and Colletotrichum truncatum;Glomerella cingluata, Glomerella gossypii, Musicillium theobromae, Plectosphaerella cucumerina, and species of the genus Verticillium, including Verticillium dahlia; species of the order Venturia, such as Venturia carpophila, Venturia effusa, Venturia inaequalis, Venturia oleaginea, and Venturia apririna; and species of the order Anthracnoseales, such as Eutypa lata, Microdochium albescens, and Microdochium variegatum. * *majus*, *Microdochium nivale*, *Microdochium paspali*, *Microdochium sorghi*, *Physalospora abdita*, species of *Rosellinia*, and *Seimatosporium mariae*; *Botryosphaeria* species, including *Botryosphaeria dothidea*; *Diplodia* species, including *Diplodia seriata*; *Dothiorella aromatica*, *Lasiodiplodia theobromae*, *Macrophoma theicola*, *Macrophomina phaseolina*, and *Phyllosticta*. ampelicida and cucurbitacearum; spores of the order Aspergillus, such as species of the genus Aspergillus, including Aspergillus flavus, Aspergillus fumigatus, Aspergillus niger and Aspergillus terreus.Species in the genus *Penicillium*, including *Penicillium digitatum*, *Penicillium expansum*, and *Penicillium italicum*; species in the order Microcystis, such as *Berkeleyomyces basicola* and *Thielaviopsis paradoxa*; species in the genus *Ceratocystis*, including *Ceratocystis fimbriata*, *Ceratocystis manginecans*, and *Ceratocystis platani*; species in the genus *Scedosporium*, including *Scedosporium apiospermum* and *Scedosporium prolificans*; and species in the order Polycystales, such as species in the genus *Elsinoe*, including *Elsinoe*. * *Ampelina* and *Elsinoe perseae*; *Leptographium*, such as *Leptographium lundbergii*, *Leptographium microsporum*, *Ophiostoma novo-ulmi*, *Ophiostoma piceae*, and species of *Sporothrix*; *Plasmomycetes*, such as *Phymatotrichopsis omnivore* and *Polyscytalum pustulans*; *Gibellina cerealis*, such as *Phyllachora maydis* and *Phyllachora pomigena*; *Griphosphaeria corticola*, *Lepteutypacupressi*, and *Pestalotia*. rhododendri); Sootyphae, such as Capnodium ramosum and Schizothyrium pomi; Spicophagus, such as species of Phialophroa;Cladosporales, including species of the genus *Cladosporium*, such as *Cladosporium oxysporum*, *Cladosporium cucumerinum*, and *Cladosporium allii-cepae*; Nephrotic Discaceales, including species of the genus *Lophodermium seditiosum* and *Naemacyclus*; Yeastales, including species of *Cephaloascus*, such as *Cephaloascus fragrans*; *Geotrichum candidum*; and species of the genus *Candida*, including *Candida glabrata*, *Candida krusei*, *Candida lusitaniae*, *Candida parapsilosis*, and *Candida albicans*. *Candida tropicalalis* and *Candida albicans*; *Candida* order, such as species of the genus *Chaetomium* and *Monosporascus cannonballus*; *Candida* class, such as *Wongia garrettii* and *Wongia griffinii*; *Taphrina* order, such as *Taphrina bullata* and *Taphrina deformans*; *Taphrina* order, such as *Ajellomyces capsulatus* and *Blastomyces dermatitidis*, and species of the genus *Coccidioides*, including *Coccidioides scabra*. *Immitis*; species of *Epidermophyton*, *Histoplasma*, *Microsporum*, *Trichophyton*, and *Paracoccidioides*, including *Paracoccioides brasiliensis*; and others such as *Hymenula cerealis*, *Petriellidum*, and *Septocyta ruborum*.

[0087] Basidiomycetes, including the order Styloides, such as *Cerotelium fici*, *Chrysomyxa arctostaphyli*, *Coleosporium ipomoeae*, *Cronartium ribicola*, *Gymnosporangium juniperi-virginianae*, and *Gymnosporangium sabinae*; species of the genus *Hemileia*, including *Hemileia vastatrix*; *Melampsora medusae*, *Melampsoralini*, *Phakopsora ampelopsidis*, *Phakopsora pachyrhizi*, and *Phragmidium*. *Mucronatum*, a genus of rust fungi, includes species of *Puccinia* such as *Puccinia allii*, *Puccinia arachidis*, *Puccinia asparagi*, *Puccinia cacabata*, *Puccinia coronata*, *Puccinia graminis*, *Puccinia helianthi*, *Puccinia hieracii*, *Puccinia hordei*, *Puccinia horiana*, *Puccinia melanocephala*, *Puccinia polysora*, *Puccinia porri*, *Puccinia recondita*, *Puccinia sorghi*, *Puccinia striiformis*, and *Puccinia striiformis*. striiformis f.sp. hordei), Puccinia striiformis f.sp.*Puccinia triticina* and wheat leaf rust; *Pucciniastrum coryli*, *Tranzschelia discolor*, and species of the genus *Uromyces*, including *Uromyces betae*, *Uromyces pisi*, and *Uromyces viciae-fabae*; *Tilletia*, such as *Neovossia moliniae*, and species of the genus *Tilletia*, including *Tilletia caries* and *Tilletia controversa*; *Sporisorium*, such as *Sporisorium*. The genus *Ustilago* includes *Ustilago reilianum* and species of the genus *Ustilago*, including *Ustilagomaydis* (maize smut), *Ustilago segetum* var. *nuda* (yellow ground smut), and *Ustilago segetum* var. *wheat*.*Urocystis tritici* and *Ustilago striiformis*; *Urocystis* order, such as species of the genus *Urocystis*, including *Urocystis agropyri*; *Agaricales* order, such as *Marasmiellus inoderma*, species of the genus *Mycena*, *Moniliophthora roreri*, and *Moniliophthora perniciosa*; *Candidae* order, such as species of the genus *Sclerotium* and species of the genus *Typhula*, including *Typhula incarnata* and *Typhula ishikariensis*; *Caulis Basidiocephalis* order, such as *Waitea*. *Rhizoctonia* species, including *Rhizoctonia cerealis*, *Rhizoctonia solani*, and *Rhizoctonia theobromae*; *Atheales*, such as *Athelia rolfsii*; *Corticium invisum* and *Laetisaria fuciformis*; *Itersonilia perplexans*; *Entyloma calendulaef.sp. dahliae* and *Entylomella microspore*; *Exobasidium vexans*; and *Phellinus*. igniarius; Russula order, such as *Stereum hirsutum*; and Tremella order, such as species of the genus *Cryptococcus*, including *Cryptococcus neoformans*.

[0088] The class Zygomycetes includes the order Mucorales, such as *Choanephora cucurbitarum*, species of the genus *Mucor*, *Rhizopus oryzae*, *Absidia corymbifera*, and *Rhizomucor pusillus*.

[0089] The class Cladosporioides includes Physoderma maydis.

[0090] And diseases caused by other species and genera closely related to those listed above.

[0091] In addition to their antifungal activity, these compositions may also exhibit activity against the following organisms: *Streptomyces scabiei* (actinomycetes); *Erwinia amylovora*, *Pectobacterium carotovorum*; *Xanthomonas* species, including *Xanthomonas axonopodis*, *Xanthomonas campestris*, *Xanthomonas citri*, *Xanthomonas oryzae*, and *Xanthomonas vesicatoria*; *Xylella fastidiosa* and *Pseudomonas* species, including *Pseudomonas syringae*; and *Polymyxa* phylum. Diseases caused by *Bacillus betae*, *Polymyxa graminis*, and *Spongospora subterranea*; as well as diseases caused by bicyclic bacteria such as *Labyrinthula zosterae*.

[0092] And diseases caused by other species and genera closely related to those listed above.

[0093] The polymorphs of the present invention disclosed herein are particularly effective against plant pathogenic fungi belonging to the following categories: Ascomycetes (e.g., *Aureobasidium*, *Cytomyces*, *Erythromyces*, *Sclerotium*, *Cytomyces*, *Uncaria*); Basidiomycetes (e.g., *Russula*, *Rhizoctonia*, *Laminaria*, *Sterilaria*, *Ustilago*); Deuteromycetes (also known as Deuteromycetes, e.g., *Botrytis*, *Helicobacter*, *Rhizoctonia*, *Fusarium*, *Syndrome*, *Cercospora*, *Alternaria*, *Pyrodactylus*, and *Pseudocercospora*); Oomycetes (e.g., *Phytophthora*, *Peronospora*, *Pseudorhyx*, *Epipremnum*, *Plasmodium*, *Plasmodium*, *Pseudorhyx*, *Pseudorhyx*, *Pseudorhyx*, *Pseudorhyx*).

[0094] In preferred embodiments, polymorphs (form A, or form B, or form C) of methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxy-prop-2-enoate, as defined herein, and mixtures thereof (listed below) can be used on the following crops and pathogens:

[0095] Preferably, polymorphs (form A, or form B, or form C) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate, as defined herein, and mixtures thereof (listed below) are suitable for controlling the following fungal diseases on soybeans and genetically modified soybeans (e.g., Bt soybeans): *Alternaria* species (Alternaria leaf spot); *Cercospora* species (Cercospora leaf spot), such as *Cercospora soybeani* or *Cercospora kikuchii*; *Colletotrichum* species (with... Sex types: *Microcystis* species (anthracnose), such as *Anthracnose spp.* or *Colletotrichum gloeosporioides*; *Cyclocarya multiflora* (leaf spot); *White Root Fungus* (sexual type: *Carya spp.*) (root rot and stem rot); *Metacarpus* species, such as *Metacarpus beanus* (damping-off); *Fusarium* species (sexual type: *Fusarium*) (wilt, root rot, or stem rot), such as *Fusarium tucauldii* and *Fusarium brasiliensis*, each causing sudden death syndrome in soybeans; *Macrophomina beanus*. Phaseolina (synonym Macropomina phaseoli) (root rot and stem rot); Forsythiae (powdery mildew); Downy mildew species (downy mildew fungi), such as *Macrophomina phaseoli*; *Macrophomina phaseoli* and *Macrophomina aegyptica* (soybean rust); *Pythium* species, such as *Macrophomina aegyptica* (sex form: *Macrophomina aegyptica*); *Pythium* species (damping-off); *Phytophthora* species (wilt, root rot, leaf rot, fruit rot, and stem rot), such as *P. megasperma* (synonym *P. sojae*); *Rhizoctonia* species, such as *Rhizoctonia solani* (root rot and stem rot); *Sclerotium* species (stem rot or white mold); *Symplocosus* species, such as *Symplocosus solani* (brown spot); *Sclerotium sclerotiorum* (…). rolfsii (synonym: Rohrafsii); species of the genus *Rhodotorula* (black root rot).

[0096] More preferably, polymorphs (form A, or form B, or form C) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate, as defined herein, and mixtures thereof (listed below) are suitable for controlling the following fungal diseases on soybeans and genetically modified soybeans (e.g., Bt soybeans): Alternaria species (Alternaria leaf spot); Cercospora species (Cercospora leaf spot), such as large... *Cercospora davidii* or *Cercospora kikuchi*; *Colletotrichum* species (sexual form: *Microcystis*) (anthracnose), such as *Anthracnose spp.* or *Colletotrichum gloeosporioides*; *Clostridium multiflorum* (leaf spot); *Metacarpa* species, such as *Metacarpa beanensis* (damping-off); *Fusarium* species (sexual form: *Fusarium*) (wilt, root rot, or stem rot), such as *Fusarium tucauldii* and *Fusarium brasiliensis*, each causing sudden death syndrome in soybeans; *Mac-* *Macrophomina phaseolina* (synonym: *Macrophomina phaseoli*) (root rot and stem rot); *Downy mildew* species (downy mildew pathogens), such as *Macrophomina aegyptium*; *Macrophomina megasperma* and *Macrophomina aegyptium* (soybean rust); *Phytophthora* species, such as *Phytophthora megasperma* (sex form: *Phytophthora megasperma*); *Phytophthora* species (wilt, root rot, leaf rot, fruit rot, and stem rot), such as *Phytophthora megasperma* (synonym: *Phytophthora sojae*); *Rhizoctonia* species, such as *Rhizoctonia solani* (root rot and stem rot); *Synthetium* species, such as *Synthetium solani* (brown spot).

[0097] Polymorphs (form A, or form B, or form C) of the compound (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester as defined herein, and mixtures thereof (listed below), are of particular importance for controlling plant pathogenic harmful fungi on soybeans and genetically modified soybeans (e.g., Bt soybeans).

[0098] The polymorphs (form A, or form B, or form C) of the compound (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester as defined herein, and mixtures thereof (listed below), are also particularly important in each case for controlling the following on soybeans and genetically modified soybeans (e.g., Bt soybeans): soybean rust fungus, American rust fungus (soybean rust), soybean causal fungus, kikuchi causal fungus, multi-branch fungus, flat-headed anthracnose fungus, sclerotium fungus, spreading forsythia, soybean shell spore fungus, northeast downy mildew fungus, or northern stem canker fungus (D. phaseolorum var. Caulivora) (soybean northern stem canker fungus).

[0099] The compositions comprising the polymorphs of the present invention disclosed herein can be used in useful plant crops including perennial and annual crops such as berry plants, such as blackberries, blueberries, cranberries, raspberries, and strawberries; cereals such as barley, corn, millet, oats, rice, rye, sorghum, triticale, and wheat; fiber plants such as cotton, flax, hemp, jute, and sisal; field crops such as sugar beets and forage beets, coffee, hops, mustard, canola, poppies, sugarcane, sunflowers, tea, and tobacco; fruit trees such as apples, apricots, avocados, bananas, cherries, citrus fruits, nectarines, peaches, pears, and plums; and grasses such as Bermuda grass, bluegrass, benjamin grass, centipede grass, yew grass, ryegrass, and St. Augustine grass. Grasses and zoysia; herbs such as basil, borage, chives, coriander, lavender, angelica, mint, oregano, parsley, rosemary, sage, and thyme; legumes such as kidney beans, lentils, peas, and soybeans; nuts such as almonds, cashews, peanuts, hazelnuts, peanuts, pecans, pistachios, and walnuts; palm trees such as oil palms; ornamental plants such as flowers, shrubs, and trees; other trees such as cocoa trees, coconut palms, olive trees, and rubber trees; vegetables such as asparagus, eggplant, broccoli, cabbage, carrots, cucumbers, garlic, lettuce, zucchini, melons, okra, onions, peppers, potatoes, squash, rhubarb, spinach, and tomatoes; and vines such as grapes.

[0100] The term “useful plant” should be understood to also include useful plants that have been transformed by the use of recombinant DNA technology to enable them to synthesize one or more selectively acting toxins, such as those known to come from toxin-producing bacteria, especially those of the genus Bacillus.

[0101] Examples of such plants are: YieldGard® (a corn variety expressing CryIA(b) toxin); YieldGardRootworm® (a corn variety expressing CryIIIB(b1) toxin); YieldGard Plus® (a corn variety expressing both CryIA(b) and CryIIIB(b1) toxins); Starlink (Corn variety, expressing Cry9(c) toxin); Herculex I® (Corn variety, expressing CryIF(a2) toxin and the enzyme phosphatidylin N-acetyltransferase (PAT) for acquiring resistance to the herbicide glufosinate); NuCOTN 33B® (Cotton variety, expressing CryIA(c) toxin); Bollgard I® (Cotton variety, expressing CryIA(c) toxin); Bollgard II® (Cotton variety, expressing CryIA(c) and CryIIA(b) toxins); VICOT (Cotton varieties expressing VIP toxin); NewLeaf® (Potato varieties expressing CryIIIA toxin); Nature-Gard® Agrisure® GT Advantage (GA21 glyphosate resistance trait), Agrisure® CB Advantage (Bt11 corn borer (CB) trait), Agrisure® RW (corn rootworm trait) and Protecta®.

[0102] Crops should be understood as those that exist naturally, are obtained through conventional breeding methods, or are obtained through genetic engineering. These include crops that possess so-called output traits, such as improved storage stability, higher nutritional value, and improved flavor.

[0103] Crops should be understood to also include those that have been conferred tolerance to herbicides (like bromobenzonitrile) or multiple classes of herbicides (such as ALS-, EPSPS-, GS-, HPPD-, and PPO- inhibitors). An example of a crop that has been conferred tolerance to imidazolinones (e.g., methoxyfenozide) through conventional breeding methods is Clearfield® Summer Canola. Examples of crops that have been conferred herbicide tolerance through genetic engineering methods include, for example, glyphosate and glufosinate-resistant corn varieties, which are commercially available under the trade names RoundupReady®, Herculex I®, and LibertyLink®.

[0104] Crops should also be understood as those that are naturally or have been conferred resistance to harmful insects. This includes plants that, for example, are capable of synthesizing one or more selectively acting toxins through the use of recombinant DNA technology, such toxins being derived from toxin-producing bacteria, as is known. Examples of toxins that can be expressed include delta-endotoxins, vegetative insecticidal proteins (Vip), insecticidal proteins from nematode-parasitic bacteria, and toxins produced by scorpions, arachnids, wasps, and fungi.

[0105] An example of a crop modified to express Bacillus thuringiensis toxin is Bt corn KnockOut® (Syngenta Seeds). An example of a crop containing more than one gene encoding insecticidal resistance and thus expressing more than one toxin is VipCot® (Syngenta Seeds). Crops or their seed material can also be resistant to multiple types of pests (a so-called superimposed transgenic event when produced through genetic modification). For example, plants can express insecticidal proteins while also being resistant to herbicides, such as Herculex I® (Dow AgroSciences, Pioneer Hi-Bred International).

[0106] Fungicidal compositions containing polymorphs as disclosed herein as active ingredients can be used to control or prevent plant pathogenic diseases on genetically modified soybean plants, especially plant pathogenic fungi (such as strophanthizobium rust).

[0107] Specifically, transgenic soybean plants expressing toxins (e.g., insecticidal proteins, such as delta-endotoxins, like Cry1Ac (Cry1Ac Bt protein)). Therefore, this can include transgenic soybean plants containing events MON87701 (disclosed in WO 2009 / 064652) and WO 2014 / 170327 (see, for example, reference to Intacta RR2 PRO). ® The paragraph on soybeans

[008] ), event MON87751 (disclosed in WO 2014 / 201235) or event DAS-81419-2 (also known as Conkesta) TM Soybeans, described in WO 2013016527.

[0108] Useful transgenic events in transgenic soybean plants that can be treated 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 (also known as Conkesta TMSoybean, described in WO 2013016527 (also known as Conkesta™ Enlist E3™ soybean, DAS-81419-2 × DAS-44406-6); 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); Event DP-356043-5 (soybean, herbicide tolerance, deposited as ATCC PTA-8287, disclosed in WO Event 2008 / 002872; 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 superimposed 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 MON87705 (soybean, improved fatty acid profile, herbicide tolerance, disclosed in WO 2008 / 002872). Event MON87751 (Lepidoptera resistance, ATCC accession number PTA-120166, disclosed in WO 2014 / 201235); Event MON87708 (Soybean, herbicide tolerance, disclosed in WO 2011 / 034704); Event MON87712 (Soybean, yield, disclosed in WO 2012 / 051199); Event MON87754 (Soybean, quality characteristics, disclosed in WO 2010 / 024976); Event MON87769 (Soybean, quality attributes, disclosed in WO 2009 / 102873); Event MON89788 (Soybean, herbicide tolerance, disclosed in WO 2006 / 130436); Event SYHT0H2 / SYN-000H2-5 (Soybean, herbicide tolerance, disclosed in WO 2006 / 130436). 2012 / 082548); Event DAS-21606-3 (Soybean, herbicide tolerance, disclosed in WO 2012 / 033794); Event 8264.44.06.Event 1 (Soybean, superimposed herbicide tolerance, disclosed in WO 2022 / 012075426); Event pDAB8291.45.36.2 (Soybean, superimposed herbicide tolerance, disclosed in WO 2012 / 075429); Event pDAB8264.42.32.1 (Soybean, superimposed herbicide tolerance, disclosed in WO2013 / 010094); Event A2704-12 (Glufosinate tolerance, disclosed in WO 2006 / 108647); Event A5547-127 (Syrhophosphatidylcholine tolerance, disclosed in WO 2006 / 108675); Event BPS-CV127-91 (Hyricide tolerance, disclosed in WO 2010 / 080829); Event GU262 (Syrhophosphatidylcholine tolerance, described in APHIS Regulatory Reference US). (98-238-01p).

[0109] Transgenic events that may be particularly useful in transgenic soybean plants treated according to the present invention include event A2704-12 (glufosinate tolerance, disclosed in WO 2006 / 108647), event A5547-127 (phosphinic acid tolerance, disclosed in WO 2006 / 108675); event GU262 (phosphinic acid tolerance, described in APHIS regulatory reference US 98-238-01p); event MON89788 (disclosed in WO 2006 / 130494 A); event DP-305423-1 (soybean, quality mark, disclosed in WO 2008 / 054747); event MON87701 (soybean, insect resistance, disclosed in WO 2009 / 064652); and event MON87705 (soybean, improved fatty acid profile, herbicide tolerance, disclosed in WO Event MON87769 (soybean, quality attributes, disclosed in WO 2009 / 102873 or US20110067141 A); Event FG72 (soybean, herbicide tolerance, disclosed in WO 2011 / 063413); Event MON87712 (soybean, yield, disclosed in WO 2012 / 051199); Event BPS-CV127-9 (soybean, herbicide tolerance, NCIMB No. 41603, disclosed in WO 2010 / 08082); Event DAS-68416-4 (soybean, herbicide tolerance, ATCC accession number PTA-10442, disclosed in WO 2011 / 066384, WO Event 2011 / 066360); Event SYHT0H2 / SYN-000H2-5 (soybean, herbicide tolerance, disclosed in WO 2012 / 082548); Event DAS-44406-6 / pDAB8264.44.06.1 (soybean, herbicide tolerance, disclosed in WO 2012 / 075426); Event MON87751 (lepidopteran resistance, ATCC accession number PTA-120166, disclosed in WO 2014 / 201235); Event MON87708 (soybean, herbicide tolerance, disclosed in WO 2011 / 034704); and Event GMB151 (also known as BCS-GM151-6, HPPD tolerance, disclosed in WO 2018119364 A1).

[0110] In addition, such a list of genetically modified events is provided by the U.S. Department of Agriculture's (USDA) Animal and Plant Health Inspection Service (APHIS) and can be found on its World Wide Web website at aphis.usda.gov.

[0111] As used herein, the term "event" refers to the name of an event associated with a unique DNA recombination event that occurs in a plant cell and is then used to produce the entire transgenic plant. Detailed information about events and related products can be found at http: / / www.isaaa.org / gmapprovaldatabase. The events listed in this article have been introduced into currently commercially available plants.

[0112] Commercially available examples of genetically modified soybeans that can preferably be treated in the method according to the invention include commercially available products, such as plant seeds, which are in ROUNDUP READY 2 XTEN ® INTACTA RR2 PRO ® VISTIVE ® GOLD, Conkesta E3 ® , Conkesta Enlist E3™, LibertyLink ® Sold or distributed under the XtendFlex® brand name.

[0113] Transgenic soybeans containing herbicide tolerance genes include, for example (but not excluding others), 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, SYHTØH2, W62, W98, FG72, and CV127.

[0114] According to one embodiment of the invention, a polymorph (form A) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein is provided for the use of a genetically modified soybean plant containing a herbicide tolerance gene. The genetically modified soybean plants containing herbicide tolerance genes include, for example (but not excluding others), 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, SYHTØH2, W62, W98, FG72, and CV127.

[0115] According to one embodiment of the invention, a polymorph (form B) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein is provided for the use of a genetically modified soybean plant containing a herbicide tolerance gene. The genetically modified soybean plants containing herbicide tolerance genes include, for example (but not excluding others), 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, SYHTØH2, W62, W98, FG72, and CV127.

[0116] According to one embodiment of the invention, a polymorph (form C) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein is provided for use in controlling plant pathogenic fungi in genetically modified soybean plants, wherein the transgenic soybean containing a herbicide tolerance gene is, for example (but not excluding others), 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, SYHTØH2, W62, W98, FG72 and CV127.

[0117] The fungicidal polymorphs and compositions disclosed herein can be used to control or prevent plant pathogenic diseases on soybean plants, especially plant pathogenic fungi (such as *Solanum spp.*). In particular, there are known superior soybean varieties in the scientific literature in which stacks of R genes conferring a certain degree of immunity or resistance to specific *Solanum spp.* have been incorporated into the plant genome; see, for example, “Fighting Asian Soybean Rust”, Langenbach C et al., Front Plant Science 7(797) 2016.

[0118] Superior plants are any plants that come from superior strains; therefore, superior plants are representative plants that come from superior varieties. Non-restricted examples of commercially available superior soybean varieties for farmers or soybean breeders include: AG00802, A0868, AG0902, A1923, AG2403, A2824, A3704, A4324, A5404, AG5903, AG6202, AG0934; AG1435; AG2031; AG2035; AG2433; AG2733; AG2933; AG3334; AG3832; AG4135; AG4632; AG4934; AG5831; AG6534; and AG7231 (Asgrow Seeds, Des Moines, Iowa, USA); BPR0144RR, BPR 4077NRR, and BPR 4390NRR (Bio Plant Research Institute). Research), Camp Point, Illinois, USA; DKB17-51 and DKB37-51 (DeKalb Genetics, DeKalb, Illinois, USA); DP 4546 RR and DP 7870 RR (Delta & Pine Land Company, Lubbock, Texas, USA); JG03R501, JG 32R606C ADD and JG 55R503C (JGL Inc.).Greencastle, Indiana, 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 Seed International, Johnston, Iowa, USA); SG4771NRR and SG5161NRR / STS (Soybean Genetics, LLC). Syngenta Seeds, Inc., Lafayette, Indiana, 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, Inc., Henderson, Kentucky, USA); Richer (Northstar Seeds, Inc., Ltd ... Ltd., Alberta, Canada; 14RD62 (StineSeed Co., Iowa, USA); or Armor 4744 (Armor Seed, LLC, Alaska, USA).

[0119] Therefore, in another preferred embodiment, the fungicidal polymorphs and compositions disclosed herein are used to control *Phyllostachys spp.* rust (including its fungicide-resistant strains, as described below) on superior soybean plant varieties, wherein the R gene stack confers a certain degree of immunity or resistance to a specific *Phyllostachys spp.* rust has been infiltrated into the plant genome. Various benefits can be anticipated from this use, such as improved bioactivity, a favorable or broader spectrum of activity (including susceptible and resistant strains of *Phyllostachys spp.* rust), increased safety, improved crop tolerance, synergistic interactions or enhancing properties, improved onset or longer persistent residual activity, reduced application frequency and / or lower application rates of the compounds and compositions required for effective control of the plant pathogen (*Phyllostachys spp.* rust), thereby enabling beneficial resistance-management practices, reduced environmental impact, and reduced operator exposure.

[0120] In certain situations, when used to control or prevent plant pathogenic diseases on soybean plants (especially any genetically modified soybean plants as described above), particularly plant pathogenic fungi (such as *Potamogeton crispus*), fungicidal compositions containing the polymorphs according to the invention and at least one additional active ingredient can exhibit synergistic interactions between the active ingredients.

[0121] Exemplary GM traits conferring enhanced ASR resistance include resistance genes encoding resistance proteins, such as: WO 2019103918 (e.g., but not limited to RG-1 (SEQ ID NO: 47) and its active variants or fragments; or R genes, such as those shown in SEQ ID NO: 28, 42, 43, 44, 45, or 46 of WO 2019103918); WO 202100878 (e.g., Rpp6907 (SEQ ID NO: 1 of WO 202100878) and its active variants or fragments); WO 2021022022 (e.g., TirA or TirB (SEQ ID NO: 11 or 16 of WO 2021022022, respectively) or their active variants or fragments); WO 2021260673 (e.g., but not limited to RG21 and / or RG22 (SEQ ID NO: 11 of WO 2021260673)). 1 or 12) or its active variants or fragments); WO 2022173659 (e.g., but not limited to RG30 (SEQ ID NO: 5 of WO 2022173659) or its active variants or fragments); WO 2022159341 (e.g., but not limited to SEQ ID NO: 1 and 148 of WO 2022159341, or its active variants or fragments); WO 2021154632 A1, WO 2021022026, WO 2021022101, US 20220135997 (e.g., but not limited to FIT1 (SEQ ID NO: 2 of US 20220135997), its active variants or fragments, or any of the paralogs or orthologs of FIT1 disclosed therein (such as SEQ ID NO: 2 of US 20220135997). 4, 6, 8, 10, 12, 14, 16, 18, or 20); US 10842097 (e.g., but not limited to CcRpp1 or its active variants or fragments, or any other resistance gene disclosed therein); WO 2022140257 (e.g., CcRpp2-R1 and / or CcRpp2-R3 (SEQ ID NO: 2 or 4 of WO 2022140257) or its active variants or fragments); resistance genes disclosed as RG31 (SEQ ID NO: 1, 3, or 4) or RG35 (SEQ ID NO: 2 or 5) in US Provisional Application No. 63 / 481627; and / or resistance genes disclosed as RG32 (SEQ ID NO: 1, 3, or 4) or RG34 (SEQ ID NO: 2 or 5) in US Provisional Application Nos. 63 / 426524 and 63 / 509586. 2, 5, 6, or 17) disclosed resistance genes; each of these documents is incorporated in its entirety by reference.

[0122] Exemplary natural traits conferring increased resistance to ASR or to pathogens from the genus Phakopsora (including species Phakopsora meibomiae) include various intervals and loci (multiple loci) associated with Rpp1, Rpp1b, Rpp2, Rpp4, Rpp5, Rpp6 and ASR resistance loci 1–16. Such natural traits can be found in, for example, WO 2009079729, US 8759607, US 8962914, WO 2008054546, US 8692054, US9091681, WO 2009132089, US 8669414, US 8796503, US 8921645, WO 2010096227, WO2010009404, WO 2021154632, US 20230067451, WO 2021022026, US 20220256795, WO2021022101, US 20220338433 A1, WO 2022173659, WO The documents 2010009404, WO 2017222827, US20210024950, WO 2021000878, US 20220380796, US 20230147114, and PCT application number PCT / US23 / 60373 are all cited in their full text.

[0123] Exemplary soybean varieties that confer increased resistance to ASR include soybean cultivars TMG 7062, TMG7161, and TMG 7261.

[0124] Other soybean varieties that confer increased resistance to ASR (caused by the rust fungus of the soybean layer) include, for example, but not limited to, TMG7368 IPRO (disclosed in WO 2009079729), TMG7062 IPRO, TMG 7063 IPRO, and TMG7061 IPRO.

[0125] Additional soybean varieties that confer increased resistance to ASR (caused by the rust fungus of the soybean and potato layer) include, for example, but not limited to, soybeans utilizing Shield Technology, such as BRS511 soybean, BRS 531 soybean, or Soy-BRS 539 (a conventional soybean utilizing Shield® and Block® technologies).

[0126] Fungicidal resistant strains of *Phyllostachys beanus* have been reported in the scientific literature, in which strains resistant to one or more fungicides from at least each of the following fungicidal action modes: sterol demethylation inhibitors (DMI), exoquinone inhibitors (QoI), and succinate dehydrogenase inhibitors (SDHI). See, for example: “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 aSDH variant with reduced SDHI sensitivity in Phakopsora pachyrhizi” Simões K et al., J Plant DisProt (2018) 125: 21-2; “Competitive fitness of Phakopsorapachyrhizi isolates with mutations in the CYP51 and CYTB genes” "Competitive adaptation of Phakopsora pachyrhizi isolates with CYP51 and CYTB gene mutations." 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 Management Sci (2016) 72: 1211-1215.

[0127] In another embodiment of the invention, a method is provided for controlling or preventing infection of genetically modified plants by plant pathogenic microorganisms, particularly plant pathogenic fungi, wherein a crystalline polymorph (form A) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate, as defined herein, is applied to the plant. Preferably, the genetically modified plant is a soybean plant. Examples of genetically modified soybean plants include, but are not 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™ 2Xtend™, Genuity® Roundup Ready 2 Yield™, herbicide-tolerant soybean lines, Optimum GAT™, Liberty Link™ soybean, Vistive Gold™, Verdeca HB4 soybean, Treus™, and Plenish™. More preferably, the genetically modified plant is a Bt soybean plant. Examples of “Bt plants” include soybean varieties sold under trade names such as: 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® RoundupReady 2 Yield™, herbicide-tolerant soybean lines, Optimum GAT™, Liberty Link™ soybean, VisiveGold™, Verdeca HB4 soybean, Treus™, and Plenish™. Even more preferably, Bt soybean plants are selected from IntactaRR2 PRO® or Conkesta Enlist E3®.

[0128] In another embodiment of the invention, a method is provided for controlling or preventing infection of genetically modified plants by plant pathogenic microorganisms, particularly plant pathogenic fungi, wherein a crystalline polymorph (form B) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate, as defined herein, is applied to the plant. Preferably, the genetically modified plant is a soybean plant. Examples of genetically modified soybean plants include, but are not 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™ 2Xtend™, Genuity® Roundup Ready 2 Yield™, herbicide-tolerant soybean lines, Optimum GAT™, Liberty Link™ soybean, Vistive Gold™, Verdeca HB4 soybean, Treus™, and Plenish™. More preferably, the genetically modified plant is a Bt soybean plant. Examples of “Bt plants” include soybean varieties sold under trade names such as: 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® RoundupReady 2 Yield™, herbicide-tolerant soybean lines, Optimum GAT™, Liberty Link™ soybean, VisiveGold™, Verdeca HB4 soybean, Treus™, and Plenish™. Even more preferably, Bt soybean plants are selected from IntactaRR2 PRO® or Conkesta Enlist E3®.

[0129] In another embodiment of the invention, a method is provided for controlling or preventing infection of genetically modified plants by plant pathogenic microorganisms, particularly plant pathogenic fungi, wherein a crystalline polymorph (form C) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate, as defined herein, is applied to the plant. Preferably, the genetically modified plant is a soybean plant. Examples of genetically modified soybean plants include, but are not 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™ 2Xtend™, Genuity® Roundup Ready 2 Yield™, herbicide-tolerant soybean lines, Optimum GAT™, Liberty Link™ soybean, Vistive Gold™, Verdeca HB4 soybean, Treus™, and Plenish™. More preferably, the genetically modified plant is a Bt soybean plant. Examples of “Bt plants” include soybean varieties sold under trade names such as: 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® RoundupReady 2 Yield™, herbicide-tolerant soybean lines, Optimum GAT™, Liberty Link™ soybean, VisiveGold™, Verdeca HB4 soybean, Treus™, and Plenish™. Even more preferably, Bt soybean plants are selected from IntactaRR2 PRO® or Conkesta Enlist E3®.

[0130] In a preferred embodiment of the invention, a method for controlling pests on soybean plants is provided, wherein the soybean plant is a Bt soybean plant, preferably selected from Bt soybean plants of Intacta RR2 PRO® or Conkesta Enlist E3®, the method being characterized by the following steps: contacting the plant, its parts, its reproductive material, pests, their food sources, habitats, or breeding grounds with a crystalline polymorph (form A) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate.

[0131] In another preferred embodiment of the invention, a method for controlling pests on soybean plants is provided, wherein the soybean plant is a Bt soybean plant, preferably selected from Bt soybean plants of Intacta RR2 PRO® or ConkestaEnlist E3®, the method being characterized by comprising the step of contacting the plant, its parts, its reproductive material, pests, their food sources, habitats, or breeding grounds with a crystalline polymorph (form B) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate.

[0132] In another preferred embodiment of the invention, a method for controlling pests on soybean plants is provided, wherein the soybean plant is a Bt soybean plant, preferably selected from Bt soybean plants of Intacta RR2 PRO® or ConkestaEnlist E3®, the method being characterized by the following steps: contacting the plant, its parts, its reproductive material, pests, their food sources, habitats, or breeding grounds with a crystalline polymorph (form C) of compound (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester.

[0133] Commercially available examples of genetically modified soybean plants that can preferably be treated according to the present invention include commercially available products, such as plant seeds, which are sold or distributed under the following 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, RoundupReady™ soybean, Roundup Ready™ 2 Xtend™, Genuity® Roundup Ready™ 2 Xtend™, Genuity® Roundup Ready 2 Yield™, herbicide-tolerant soybean lines, Optimum GAT™, LibertyLink™ soybean, Vistive Gold™, Verdeca HB4 soybean, Treus™, or Plenish™.

[0134] Commercially available examples of Bt soybean plants that can preferably be treated according to the present invention include commercially available products, such as plant seeds, which are sold under the following 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® RoundupReady 2 Yield™, herbicide-tolerant soybean lines, Optimum GAT™, Liberty Link™ soybean, VistiveGold™, Verdeca HB4 soybean, Treus™, or Plenish™.

[0135] Preferably, the genetically modified soybean plants that can be treated according to the present invention are selected from Intacta RR2 PRO® or Conkesta Enlist E3®.

[0136] In another embodiment of the invention, the use of a crystalline polymorph (form A) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein is provided for controlling plant pathogenic fungi (preferably, *Potato rust*) in genetically modified plants. 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 RR2PRO® or Conkesta Enlist E3®.

[0137] In another embodiment of the invention, the use of a crystalline polymorph (form B) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein is provided for controlling plant pathogenic fungi (preferably, *Potato rust*) in genetically modified plants. 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 RR2PRO® or Conkesta Enlist E3®.

[0138] In another embodiment of the invention, the use of a crystalline polymorph (form C) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein is provided for controlling plant pathogenic fungi (preferably, *Potato rust*) in genetically modified plants. 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 RR2PRO® or Conkesta Enlist E3®.

[0139] As used herein, the terms "genetically modified plant" or "genetically modified soybean plant" refer to a plant or soybean plant whose genetic material has been altered in a manner not naturally occurring through mating and / or natural recombination. These plants are also known as transgenic or genetically engineered plants. Genetic modification of plants involves adding a specific piece of DNA to the plant's genome, thereby conferring new or different characteristics. This can include altering how the plant grows or making it resistant to specific diseases. Examples of genetically modified soybean plants are available under the following 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® RoundupReady 2 Yield™, herbicide-tolerant soybean lines, Optimum GAT™, Liberty Link™ soybean, VistiveGold™, Verdeca HB4 soybean, Treus™, Plenish™.

[0140] As used herein, the term "Bt soybean plant" refers to a soybean plant that has been genetically engineered to produce insecticidal proteins similar to those naturally produced by the bacterial species Bacillus thuringiensis, such as those produced by the genes CrylA(a), CrylA(b), CrylA(c), CryllA, CryllA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb, and CrylF, and combinations thereof. These soybeans, genetically engineered to produce the same toxins as Bacillus thuringiensis (Bt) in each cell of the plant (with the aim of protecting soybeans from harmful organisms), are referred to herein as "Bt soybeans." Example Bt soybean plants are Intacta RR2 PRO® or Conkesta Enlist E3®.

[0141] Polymorphs (form A, or form B, or form C) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate, as defined herein, can be used in their unmodified form, or preferably in combination with adjuvants conventionally used in the field of formulations. For this purpose, they can be conveniently formulated in known manner as emulsifiable concentrates, coating pastes, directly sprayable or dilutable solutions or suspensions, diluted emulsions, wettable powders, soluble powders, dusts, granules, and encapsulating agents, for example, in polymeric substances. The method of application, such as spraying, atomizing, dusting, spreading, smearing, or watering, is selected according to the intended purpose and the prevailing environment for the type of composition. The composition may also contain additional adjuvants, such as stabilizers, defoamers, viscosity modifiers, binders or thickeners, and fertilizers, micronutrient donors, or other formulations for achieving specific effects.

[0142] Suitable carriers and adjuvants, for example for agricultural uses, can be solid or liquid and are useful in formulation techniques, such as natural or recycled minerals, solvents, dispersants, wetting agents, thickeners, binders, or fertilizers. Such carriers are described, for example, in WO 1997 / 33890.

[0143] Suspension concentrates are aqueous formulations in which finely dispersed solid particles of an active compound are suspended. These formulations contain anti-settling agents and dispersants, and may further contain wetting agents to enhance activity, as well as antifoamers and crystal growth inhibitors. When used, these concentrates are diluted in water and are typically applied as a spray to the area to be treated. The amount of active ingredient can range from 0.5% to 95% of the concentrate.

[0144] Wettable powders are finely dispersed granules that are easily dispersed in water or other liquid carriers. These granules contain active ingredients retained in a solid matrix. Typical solid matrices include bleaching clay, kaolin, silica, and other easily wettable organic or inorganic solids. Wettable powders typically contain 5% to 95% active ingredient plus small amounts of wetting agents, dispersants, or emulsifiers.

[0145] Emulsifiable concentrates are homogeneous liquid compositions dispersible in water or other liquids and may consist entirely of an active compound and a liquid or solid emulsifier, or may contain a liquid carrier such as xylene, heavy aromatic naphtha, isophorone, and other non-volatile organic solvents. In use, these concentrates are dispersed in water or other liquids and are typically applied as a spray to the area to be treated. The amount of active ingredient can range from 0.5% to 95% of the concentrate.

[0146] Granular formulations consist of both extrudates and coarser granules, and are typically applied undiluted to the area requiring treatment. Typical carriers used in granular formulations include sand, bleaching clay, attapulgite clay, bentonite, montmorillonite, vermiculite, perlite, calcium carbonate, brick, pumice, pyrophyllite, kaolin, dolomite, plaster, wood flour, crushed corn cobs, crushed peanut shells, sugar, sodium chloride, sodium sulfate, sodium silicate, sodium borate, magnesium oxide, mica, iron oxide, zinc oxide, titanium oxide, antimony oxide, cryolite, gypsum, diatomaceous earth, calcium sulfate, and other organic or inorganic materials that absorb or can be coated with active compounds. Granular formulations typically contain 5% to 25% of the active ingredient, which may include surfactants such as heavy aromatic naphtha, kerosene, and other petroleum fractions, or vegetable oils; and / or binders such as dextrin, gum, or synthetic resins.

[0147] Powders are free-flowing mixtures of active ingredients and finely dispersed solids (such as talc, clay, flour, and other organic and inorganic solids that act as dispersants and carriers).

[0148] Active ingredients (such as polymorphs of methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxy-prop-2-enoate as defined herein, or mixtures thereof with components (B) and / or (C)) may also be contained in microcapsules. Microcapsules contain the active ingredient within a porous carrier. This allows the active ingredient to be released into the environment in a controlled amount (e.g., slowly). Microcapsules typically have a diameter of 0.1 to 500 micrometers. They contain an amount of active ingredient that is approximately 25% to 95% by weight of the capsule. These active ingredients may be in the form of a monolithic solid, fine particles in a solid or liquid dispersion, or a suitable solution. The encapsulating membrane may contain, for example, natural or synthetic rubber, cellulose, styrene / butadiene copolymer, polyacrylonitrile, polyacrylate, polyester, polyamide, polyurea, polyurethane, or chemically modified polymers, as well as starch xanthate, or other polymers known to those skilled in the art. Alternatively, very fine microcapsules can be formed in which the active ingredient is contained in the form of finely dispersed particles in the solid matrix of the base substance, but these microcapsules themselves are not encapsulated.

[0149] Microcapsules are typically droplets or granules of an active ingredient encapsulated in an inert, porous shell that allows the encapsulated material to escape into the environment at a controlled rate. The diameter of the encapsulated droplets is typically 1 to 50 micrometers. The encapsulated liquid typically constitutes 50% to 95% of the capsule weight and may contain a solvent in addition to the active compound. Encapsulated granules are typically porous particles in which a porous membrane seals the pores, retaining the active species in liquid form within the pores. The diameter of the granules typically ranges from 1 millimeter to 1 centimeter, and preferably from 1 to 2 millimeters. Granules are formed by extrusion, aggregation, or pelletizing, or are naturally occurring. Examples of such materials are vermiculite, sintered clay, kaolin, attapulgite clay, sawdust, and carbon granules. Shell or membrane materials include natural and synthetic rubbers, fibrous materials, styrene-butadiene copolymers, polyacrylonitrile, polyacrylates, polyesters, polyamides, polyureas, polyurethanes, and starch xanthates.

[0150] Other useful formulations for agrochemical applications include simple solutions of the active ingredient in solvents such as acetone, alkylated naphthalene, xylene, and other organic solvents, in which the active ingredient is completely dissolved at the desired concentration. Pressurized sprays can also be used, in which the active ingredient is dispersed in a finely dispersed form due to the evaporation of low-boiling-point dispersants, solvents, and carriers.

[0151] Suitable agricultural adjuvants and carriers useful for formulating the compositions of the present invention among the above-described formulation types are well known to those skilled in the art.

[0152] Suitable liquid carriers include, for example, water, toluene, xylene, naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenyl, amyl acetate, 2-butanone, chlorobenzene, cyclohexane, cyclohexanol, alkyl acetate, diacetone alcohol, 1,2-dichloropropane, diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycol rosinate, diethylene glycol butyl ether, diethylene glycol ethyl ether, diethylene glycol methyl ether, N,N-dimethyl... Formamide, dimethyl sulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether, dipropylene glycol dibenzoate, dipropylene glycol (diproxitol), alkylpyrrolidone, 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, glyceryl diacetate, glyceryl monoester Acetates, triacetin, hexadecane, hexanediol, isoamyl acetate, isobornyl acetate, isooctane, isophorone, cumene, isopropyl myristate, lactic acid, laurylamine, isopropylidene acetone, methoxypropanol, methyl isopentyl ketone, methyl isobutyl ketone, methyl lauryl ketone, methyl octanoate, methyl oleate, dichloromethane, m-xylene, n-hexane, n-octylamine, stearic acid, octylamine acetate, oleic acid, oleylamine, o-xylene, benzene Phenols, polyethylene glycol (PEG400), propionic acid, propylene glycol, propylene glycol monomethyl ether, p-xylene, toluene, triethyl phosphate, triethylene glycol, xylenesulfonic acid, paraffin wax, mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, methanol, ethanol, isopropanol, and higher molecular weight alcohols (such as pentanol, tetrahydrofurfuryl alcohol, hexanol, octanol, etc.), ethylene glycol, propylene glycol, glycerol, and N-methyl-2-pyrrolidone. Water is typically used as the carrier for diluting concentrates.

[0153] Suitable solid carriers include, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, diatomaceous earth, chalk, lime, calcium carbonate, bentonite, bleaching clay, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell powder, and lignin.

[0154] A wide range of surfactants are advantageously used in the liquid and solid compositions, especially those designed to be diluted with a carrier prior to application. These agents typically constitute 0.1% to 15% by weight of the formulation when used. They can be anionic, cationic, nonionic, or polymeric in nature and can be used as emulsifiers, wetting agents, suspending agents, or for other purposes. Typical surfactants include alkyl sulfates, such as diethanolammonium lauryl sulfate; alkyl aryl sulfonates, such as calcium dodecylbenzenesulfonate; alkylphenol-epoxide addition products, such as nonylphenol-C.sub.18 ethoxylate; alcohol-epoxide addition products, such as tridecyl alcohol-C.sub.16 ethoxylate; soaps, such as sodium stearate; alkyl naphthalene sulfonates, such as sodium dibutylnaphthalene sulfonate; salts of dialkyl sulfosuccinates, such as sodium di(2-ethylhexyl)sulfosuccinate; sorbitol esters, such as sorbitol oleate; quaternary ammonium chloride, such as lauryltrimethylammonium 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 phosphates.

[0155] Other adjuvants commonly used in agricultural compositions include crystallization inhibitors, viscosity modifiers, suspending agents, spray droplet modifiers, pigments, antioxidants, foaming agents, defoamers, opacifiers, compatibility agents, masking agents, neutralizers and buffers, corrosion inhibitors, dyes, flavor enhancers, spreading agents, penetration enhancers, micronutrients, softeners, lubricants, and fixatives.

[0156] Furthermore, other biocidal active ingredients or compositions may be combined with the compositions of the present invention and used in the methods of the present invention, and applied simultaneously or sequentially with the compositions of the present invention. When applied simultaneously, these additional active ingredients may be formulated or mixed together with the compositions of the present invention, for example, in a spray can. These additional biocidal active ingredients may be fungicides, herbicides, insecticides, bactericides, acaricides, nematicides, and / or plant growth regulators.

[0157] The pesticides referred to in this article by their common names are, for example, those known from "The Pesticide Manual", 15th edition, British Crop Protection Council 2009.

[0158] Furthermore, the compositions of the present invention can also be administered in combination with one or more systemically acquired resistance inducers (“SAR” inducers). SAR inducers are known and described, for example, in U.S. Patent No. 6,919,298, and include, for example, salicylates and the commercial SAR inducer aramid-phenyl-S-methyl.

[0159] Polymorphs (form A, or form B, or form C) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate, as defined herein, are typically used in the form of agrochemical compositions and can be applied simultaneously or sequentially to the crop area or plants to be treated, along with other compounds. These other compounds may, for example, be fertilizers or micronutrient donors or other formulations that influence plant growth. They may also be selective or non-selective herbicides, and insecticides, fungicides, bactericides, nematicides, molluscicides, or mixtures of several of these formulations, if desired, along with additional carriers, surfactants, or application-promoting adjuvants commonly used in the field of formulations.

[0160] The polymorph of (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxy-prop-2-enoic acid methyl ester (form A, or form B, or form C) as defined herein may be used in the form of a (fungicide) composition for controlling or protecting against the effects of plant pathogenic microorganisms, the composition comprising, as an active ingredient, the polymorph as defined herein (in free form or in the form of an agrochemically available salt) and at least one of the above-described adjuvants.

[0161] Therefore, the present invention provides a composition, preferably a fungicidal composition, comprising a polymorph (form A, or form B, or form C) of methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxy-propane-2-enoate as defined herein, an agriculturally acceptable carrier, and optionally an adjuvant. An agriculturally acceptable carrier is, for example, a carrier suitable for agricultural use. Agricultural carriers are well known in the art. Preferably, the composition may comprise at least one or more pest-killing compounds, such as additional fungicidal active ingredients besides the polymorph (form A, or form B, or form C) of methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxy-propane-2-enoate as defined herein.

[0162] Polymorphs of methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxy-prop-2-enoate (form A, or form B, or form C), as defined herein, may be the sole active ingredient in a composition, or may be blended with one or more additional active ingredients, such as pest control agents, fungicides, synergists, herbicides, or plant growth regulators, where appropriate. In some cases, additional active ingredients can produce unexpected synergistic activity.

[0163] Examples of suitable additional active ingredients include the following: acycloamino acid fungicides, aliphatic nitrogen fungicides, amide fungicides, aniline fungicides, antibiotic fungicides, aromatic fungicides, arsenic-containing fungicides, arylphenyl ketone fungicides, benzamide fungicides, benzoylaniline fungicides, benzimidazole fungicides, benzothiazole fungicides, phytofungicides, bridging biphenyl fungicides, carbamate fungicides, phenyl carbamate fungicides, conazole fungicides, copper fungicides, diformimide fungicides, dinitrophenol fungicides, dithiocarbamate fungicides, dithiopentane fungicides, furfural fungicides, furfurylamide fungicides, furfurylaniline fungicides, hydrazide fungicides, imidazole fungicides, mercury fungicides, morpholine fungicides, and organophosphate fungicides. Organotin fungicides, oxathiin fungicides, oxazole fungicides, thiophene fungicides, polysulfide fungicides, pyrazole fungicides, pyridine fungicides, pyrimidine fungicides, pyrrole fungicides, quaternary ammonium fungicides, quinoline fungicides, quinone fungicides, quinoxaline fungicides, agaricone fungicides, sulfonanilide fungicides, thiadiazole fungicides, thiazolidine fungicides, thiocarbamate fungicides, thiophene fungicides, triazine fungicides, triazole fungicides, triazolopyrimidine fungicides, urea fungicides, valinamide fungicides, and zinc fungicides.

[0164]

[0165] In preferred embodiments, suitable additional active ingredients are selected from the group consisting of: benzo[a]fluopyram, fluopyram, fluopyram hydroxylamine, pyraclostrobin, fluopyram, pyraclostrobin, fluopyram, bifenthionil, difenoconazole, cyproconazole, tebuconazole, hexaconazole, prothioconazole, propiconazole, fluopyram, tebuconazole, fluopyram, 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propionate, methyl 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1,2,4-triazol-1-ylmethyl)cyclopentanecarboxylate, fenazol, chlorfluazol, Azoxystrobin, paclobutrazol, azoxystrobin, pyraclostrobin, pyraclostrobin, metalaxyl-M, benzyl sulfide, butyl morpholine, pyraclostrobin, spirocyclam, mancozeb, chlorothalonil, captan, copper oxychloride, copper hydroxide, sulfur, fluoxadixyl acetonide, isopropyl quinoline, quinoline, dimethomorph, fluazinam, fluazinam, fosetyl-aluminum, aramid-S-methyl, tebufenozide, indopyr, fluoxadixyl, isopropyl fluopyram, tetrazolium, pyridaben, methyl arylpyridinium, fluoxadixyl, isopropyl fluopyram, iprodione, carbendazim, cyclophosphamide, prochloraz, calcium cyclophosphamide, Melaleuca alternifolia oil (extract of Melaleuca alternifolia from tea plant (as Timorx)) Gold® is commercially available and is a broad-spectrum plant fungicide, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methylformamidin, trifluoropyridinamide, calcium phosphonate, cis-jasmone, anti-rot ester-ethyl, glyphosate, 2,4-D (2,4-dichlorophenoxyacetic acid), and thiamethoxam.

[0166] The compounds of the present invention can also be used in combination with anthelmintic agents. Such anthelmintic agents include compounds selected from macrolides, such as ivermectin, abamectin, emamectin, irinotecan, dolactin, silacritin, moxicritin, nemactin, and milbemycin derivatives, as described in EP-357460, EP-444964, and EP-594291. Additional anthelmintic agents include semi-synthetic and biosynthetic ivermectin / milbemycin derivatives, such as those described in US-5015630, WO-9415944, and WO-9522552. Additional anthelmintic agents include benzimidazoles, such as albendazole, canbendazole, fenbendazole, flubendazole, mebendazole, oxifendazole, oxifendazole, parbendazole, and other members of this class. Additional anthelmintics include imidazothiazoles and tetrahydropyrimidines, such as tetraimidazole, levamisole, pamoate, octetil, or molentaxel. Additional anthelmintics include trematodes, such as triclofenac and closulon, and tapeworms, such as praziquantel and esetel.

[0167] The polymorphs of the present invention can be used in combination with derivatives and analogs of paraherquamide / marcfortine anthelmintics and antiparasitic oxazoline agents (such as those disclosed in US-5478855, US-4639771 and DE-19520936).

[0168] The polymorphs of the present invention can be used in combination with derivatives and analogs of dioxomorphic antiparasitic agents of the general class as described in WO 9615121, and can also be used in combination with cyclic ester peptides with anthelmintic activity (such as those described in WO 9611945, WO 9319053, WO 9325543, EP-626375, EP-382173, WO-9419334, EP-382173 and EP-503538).

[0169] The polymorph of the present invention can be used in combination with other ectoparasite-killing agents such as fipronil; pyrethroids; organophosphates; insect growth regulators such as clofenuron; molluscin agonists such as tebufenozide; neonicotinoids such as imidacloprid.

[0170] The polymorphs of the present invention can be used in combination with terpene alkaloids, such as those described in WO 95 / 19363 or WO 04 / 72086, and especially the compounds disclosed therein.

[0171] Other examples of such bioactive compounds that can be used in combination with the compounds of the present invention include, but are not limited to, the following:

[0172] Organophosphates: Acetaminophen, Methylpyridinium phosphate, Ethyl glutathione, Methyl glutathione, Bromothione, Ethyl Bromothione, Thiophanate, Chlorethoxyphos, Chlorpyrifos, Chlorfenapyr, Demeton-methyl, Demeton-S-methyl sulfone, Chlorimide, Diazinon, Dichlorvos, Phosphate, Dimethoate, Ethiophos, Ethiophos, Ethiophos, Ethylpyridinium phosphate, Valdex, Benzylphos, Fenitrothion, Fonsophos, Fenthion, Pyralidoxime, Terbufos, Ango, Thiazolephos, Heptenphos, Chlorpyrifos, Isoprophos, Isoxazolphos Malathion, chlorfenapyr, methamidophos, chlorpyrifos, methyl parathion, methamidophos, phosmet, dibromophos, omethoate, sulfoxide, paraoxon, parathion, methyl parathion, phosmet, phosmet, phosmet, phosmet, phosmet, phosmet, phorate, phorate, phoxim, pyrimidine, methyl pyrimidine, profenofos, proetamphos, pyrazophos, pyrazophos, pyridazin, quinalphos, thiophanate-methyl, dithion, terbufos, butylpyrimidine, chlorpyrifos, thimeton, triazophos, trichlorfon, aphidicide.

[0173] Carbamates: Carbofuran, Aldicarb, 2-sec-butylphenylmethylcarbamate, Propylene carbofuran, Carbofuran, Butyl carbofuran, Dichlorvos, Ethylbenzylcarbide, Phenoxycarbide, Fenthiocarb, Furazolidone, HCN-801, Isopropylcarbide, Indomethacin, Methomyl, 5-Methyl-m-isopropylphenylbutynyl (methyl)carbamate, Apicarb, Pyriproxycarb, Prochloraz, Thiamethoxam, Dichlorvos, Apicarb, UC-51717.

[0174] Pyrethroids: Flufenoxuron, Propyrethrin, Alphametrin, 5-Benzyl-3-furanylmethyl(E)-(1R)-cis-2,2-dimethyl-3-(2-oxothiacyclopentan-3-ylidenemethyl)cyclopropanecarboxylate, Bifenthrin, β-Cypermethrin, Flufenoxuron, α-Cypermethrin, β-Cypermethrin, Bioallethrin, Bioallethrin ((S)-cyclopentyl isomer), Biobenzylfuran, Bifenthrin, NCI-85193, Cypermethrin, Trifluralin Esters, cythithrin, deltamethrin, dextromethorphan, cypermethrin, fenvalerate, fenvalerate, pendimethalin, cypermethrin, fenvalerate, flufenoxuron, flufenoxuron, deltamethrin (D isomer), deltamethrin, deltamethrin, λ-deltamethrin, permethrin, deltamethrin, dextromethorphan, pyrethrin (natural product), benzalkonium chloride, deltamethrin, tetrafluorobenzene, θ-cypermethrin, flusilylpyrethrin, t-flumethinylpyrethrin, heptamethrin, tetrabromopyrethrin, ζ-cypermethrin.

[0175] Arthropod growth regulators: a) Chitosan synthesis inhibitors: Benzoylurea: diflubenzuron, chlorfenapyr, pyridaben, flufenoxuron, flufenuron, flufenuron, chlorfenuron, flufenuron, flufenuron, chlorfenapyr, thiamethoxam, bensulfuron, thiamethoxam, etoxazole, chlorfenapyr; b) Decacitonin antagonists: chlorfenapyr, methoxyfenozide, tebufenozide; c) Juvenile hormone analogs: pyriproxyfen, tebufenozide (including S-tebufenozide), phenoxycarb; d) Lipid biosynthesis inhibitors: spirodiclofen.

[0176] Other antiparasitic agents: Acaricide, Amitraz, AKD-1022, ANS-118, Azadirachtin, Bacillus thuringiensis, Cypermethrin, Bifenazate, Acaricide, Bromopropylate, BTG-504, BTG-505, Toxaphene, Dimethoate, Ethylmethrin, Amitraz, Bromniflora, Cyclodinafop-methyl, Thiamethoxam, Dimethoate, Diacloden, Difenoconazole, DBI-3204, Dimethoate, Dihydroxybenzene Methyl dihydroxypyrrolidine, fenpyroximate, fenpyroximate, endosulfan, acetamiprid, permethrin, quinclorac, flumite, MTI-800, abamectin, pyrimethanil, flufenoxuron, deltamethrin, flufenoxuron, trifluralin, fluproxyfen, halofenprox, flufenoxuron, IKI-220, sodium silicate, NC-196, Indian mint (neem) guard), nidinorterfuran, acetamiprid, SD-35651, WL-108477, acetamiprid, chlorfenapyr, protrifenbute, pymetrozine, pyridaben, pyrimethanil, NC-1111, R-195, RH-0345, RH-2485, RYI-210, S-1283, S-1833, SI-8601, flusilyl ester, silomadine, spinosad, pymetrozine, tetrachlorfon, tetrachlorfon, thiamethoxam, cypermethrin, thiamethoxam, azoxystrobin, pymetrozine, spinosad, triacetin, pyridaben, vertalec, YI-5301.

[0177] Biological agents: Bacillus thuringiensis ssp aizawai, Bacillus thuringiensis kurstaki, Bacillus thuringiensis δ endotoxin, baculoviruses, entomopathogenic bacteria, viruses and fungi.

[0178] Bactericides: chlortetracycline, oxytetracycline, streptomycin.

[0179] Other biological agents: Enflufloxacin, febantal, pentxacillin, meloxicam, cephalexin, kanamycin, pimoxendan, clenbuterol, omeprazole, tiamulin, benazepril, pyriprole, cefquinoxime, florfenicol, buserelin, cefotaxime, tolazoline, ceftiofur, carbofenoxuron, meflurane, praziquantel, triclobenzazole.

[0180] The following mixtures of polymorphs and active ingredients are preferred, wherein TX represents crystalline polymorph form A of compound (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester, or crystalline polymorph form B of compound (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester, or crystalline polymorph form C of compound (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester:

[0181] Choose compounds from the following groups of substances:

[0182] (4E,10Z)-Tetradecano-4,10-dienyl acetate + TX; (7E,9Z)-Dodeca-7,9-dien-1-yl acetate + TX; (E)-6-methylhept-2-en-4-ol + TX; (E)-dec-5-en-1-yl acetate and (E)-dec-5-en-1-ol + TX; (E)-Tetaneca-4-en-1-yl acetate + TX; (S)-Bio-Allenyl acetate + TX; (Z)-Dodeca-7-en-1-yl acetate + TX; (Z)-Hexadecano-11-en-1-yl acetate + TX; (Z)-Hexadecano-11-enal + TX; (Z)-Hexadecano-13-en-11-yn-1-yl acetate + TX; (Z)-Eicosateca-13-en-10-one + TX TX; (Z)-Tetradecano-7-en-1-al + TX; (Z)-Tetradecano-9-en-1-ol + TX; (Z)-Tetradecano-9-en-1-ylacetate + TX; 1,1-bis(4-chlorophenyl)-2-ethoxyethanol + TX; 1-(2-chlorophenyl)-3,3-dimethyl-2-(1,2,4-triazol-1-ylmethyl)but-2-ol + TX; 1-(5-bromo-2-pyridyl)-2-(2,4-difluorophenyl)-1,1-difluoro-3-(1,2,4-triazol-1-yl)prop-2-ol + TX; 1-hydroxy-1H-pyridine-2-thione + TX; 1-methylcyclopropene + TX; 1-naphthylacetamide + TX; 1-naphthylacetic acid + TX; 2,2-dichlorovinyl-2-ethylsulfinylethylmethyl phosphate + TX; 2,4-D +TX; 2,4-DB + TX; 2,6-Dichloro-N-(4-trifluoromethylbenzyl)benzamide + TX; 2-(1,3-dithiopentane-2-yl)phenyl dimethylcarbamate + TX; 2-(2-butoxyethoxy)ethyl piperate + TX; 2-(4,5-dimethyl-1,3-dioxolane-2-yl)phenyl methylcarbamate + TX; 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindane-4-yl)pyridine-3-carboxamide + TX; 2-(octylthio)-ethanol + TX; 2-bromo-2-bromomethylglutaronitrile + TX; 2-chlorovinyl diethyl phosphate + TX; 2-imidazolinone + TX; 2-methyl(prop-2-ynyl)aminophenyl methylcarbamate + TX; 2-cyanothioethyl lauryl ester + TX; 3-(4-chlorophenyl)-5-methylrhodanine + TX; 3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindane-4-yl]pyrazole-4-carboxamide + TX; 3-(difluoromethyl)-N-(7-fluoro-1,1,3,3-tetramethyl-indane-4-yl)-1-methyl-pyrazole-4-carboxamide + TX;3-(difluoromethyl)-N-(7-fluoro-1,1,3,3-tetramethyl-indan-4-yl)-1-methyl-pyrazole-4-carboxamide + TX; 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine + TX; 3-methyl-1-phenylpyrazole-5-yldimethyl-carbamate + TX; 3-phenylphenol + TX; 4,5-dichlorodithiol-3-one + TX; 4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazine-3-carboxynitrile + TX; 4-(2-bromo-4-fluoro-phenyl)-N-(2-chloro-6-fluoro-phenyl)-2,5-dimethyl-pyrazole-3-amine + TX; 4-(quinoxalo-2-ylamino)benzenesulfonamide + TX; 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile + TX; 4-chloro-2-(2-chloro-2-methyl-propyl)-5-[(6-iodo-3-pyridyl)methoxy]pyridazin-3-one + TX; 4-CPA + TX; 4-methyl(prop-2-ynyl)amino-3,5-xylylmethylcarbamate + TX; 4-methylnon-5-ol and 4-methylnon-5-one + TX; 4-phenylphenol + TX; 5-(1,3-benzodioxane-5-yl)-3-hexylcyclohex-2-enone + TX; 5-amino-1,3,4-thiadiazole-2-thiol + TX; 5-fluoro-2-(p-tolylmethoxy)pyrimidin-4-amine + TX; 5-hydroxy-6-methyl-4-(((E)-pyridin-3-ylmethylene)amino)-4,5-dihydro-1,2,4-triazine-3(2H)-one + TX; 5-methyl-6-thio-1,3,5-thiadiazine-3-ylacetic acid + TX; 8-hydroxyquinoline sulfate + TX; 11-ethyl-10,12-dioxo-2,5,8-trithia-4,11-diazatricyclo[7.3.0.03,7]dodec-1(9),3,6-trien-6-carboxynitrile + TX; 14-methyloctadec-1-ene + TX; [(9Z,11E)-tetradec-9,11-dienyl]acetate + TX; [(Z)-dodec-9-enyl]acetate + TX; Abamectin + TX; Acetaminophen + TX; Acaricide + TX; Acetamiprid + TX; Asethirimol + TX; Acetaminophen + TX; Aramacin + TX; Aramacin-S-methyl + TX; Flufenoxuron + TX; Cotton Brown Leaf Roller GV + TX; Agrobacterium radiata + TX; Cotton Booster + TX; Albendazole + TX; Aldicarb + TX; Propyrethroid + TX; Aloxane + TX; Allyl alcohol + TX; Dichlorvos + TX;α-Degenetin + TX; α-Polytetramine + TX; Species of *Amblyomyces* + TX; Azoxystrobin + TX; Cypermethrin + TX; Sulfamethoxam + TX; Phosphatidylcholine + TX; Mefenoxam + TX; Indoxam + TX; Ammonium phosphate + TX; Ammonium phosphate oxalate + TX; Amitraz + TX; Neonicotinic acid + TX; Celery cutworm NPV + TX; *Protoceratops spp.* + TX; Pyrimidine + TX; Dimethoate + TX; Fluphenyladenine + TX; Anthraquinone + TX; Anthraquinone + TX; Amoxicillin + TX; Short-spur aphid wasp + TX; Cotton aphid parasitoid wasp + TX; Aphid gall midge + TX; Ethyl chlorpyrifos + TX; Nystatin A + TX; Alfalfa silver-striped cutworm NPV + TX; Abamectin B1a + TX; Azaconazole + TX; Azadirachtin A + TX; pyrazosulfuron + TX; methyl pyridaben + TX; ethyl glutathion + TX; methyl glutathion + TX; thiram + TX; azoxystrobin + TX; Bacillus spores (Ned) + TX; Bacillus thuringiensis + TX; Bacillus thuringiensis δ-endotoxin + TX; Bacillus thuringiensis subsp. sarsaparilla + TX; baculovirus + TX; pyrethrin + TX; Beauveria bassiana + TX; benzalkonium chloride + TX; benzalkonium chloride + TX; benzoyl + TX; benzalkonium chloride + TX; benzoyl + TX; benzalkonium chloride + TX; benzoyl + TX; benzoyl + TX; benzoyl + TX; β-cyhalothrin + TX; β-cypermethrin + TX; benzyl thiazoxazine + TX TX; Bifenazate + TX; Bifenthrin + TX; Acaricide + TX; Bio-allethrin + TX; Bio-cypermethrin + TX; Bio-permethrin + TX; Bio-benzoxyfen + TX; Diflubenzuron + TX; Diflubenzuron + TX; Bifenthrin + TX; Bifenazate + TX; Blorothalonil + TX; Borax + TX; Bordeaux mixture + TX; Cypermethrin + TX; Bromodiphenyl ether + TX; Bromophos + TX; Bromophos-ethyl + TX; Fenoxac + TX; Difenoconazole + TX; Ethylpyridinium sulfonate + TX; Thiazidone + TX; Buseretin + TX; Buschurr + TX TX; N-[6-[[(Z)-[(1-methyltetrazole-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate butyl-3-yne ester + TX; pyrimethanil + TX; pyrimethanil + TX; methyl ethyl ketone + TX;Butyl phosphate + TX; DEET + TX; Butoxyl (polypropylene glycol) + TX; Butanone sulfonate + TX; Butylamine + TX; Thiophanate + TX; Calciferol + TX; Calcium phosphate + TX; Calcium polysulfide + TX; Canbendazole + TX; Captan + TX; Carbendazim + TX; Chlorfenapyr + TX; Carbaryl + TX; Carbendazim + TX; Carbendazim Hydrochloride + TX; Carbofuran + TX; Thiocarbofuran + TX; Carbofuran + TX; Carbofuran + TX; Cyproterone + TX; Pyralidone + TX; Pyralidone Hydrochloride + TX; Cephalexin + TX; Cefotaxime + TX; Ceftriaxone + TX; Cefquinoline + TX; Ceftiofur + TX; Cestex + TX; Servadine + TX; Acaricide + TX; Chitosan + TX; Chlorpheniramine + TX; Chloralose + TX; Chlorantraniliprole + TX; Acaricide + TX; Amitraz + TX; Ethephon + TX; Phosphorus oxychloride + TX; Brofenoxam + TX; Chlorfenapyr + TX; Tetramethrin + TX; Chlorfenapyr + TX; Difenoconazole + TX; Chlormethazine + TX; Chlorpyrifos + TX; Chlorpyrifos + TX; Chlorpyrifos + TX; Chlorpyrifos + TX; Chlorpyrifos-methyl + TX; Chlortetracycline + TX; Chlorpyrifos + TX; Ethiophanate-methyl + TX; Cholecalciferol + TX; Cyclofenac + TX; Lacewing + TX; Ciprofloxacin + TX; Ciprofloxacin I + TX TX; Cucurbitacin II + TX; cis-jasmone + TX; cis-resmethrin + TX; cismethrin + TX; clenbuterol + TX; glycyrrhizin + TX; terbuprofen + TX; benzimidazin + TX; chlorfluazuron + TX; thiamethoxam + TX; chlorpyrifos (acetamide) + TX; dodecadienol + TX; copper acetate + TX; copper hydroxide + TX; copper naphthenate + TX; copper octanoate + TX; copper oleate + TX; copper oxide + TX; copper oxychloride + TX; copper silicate + TX; copper sulfate + TX; copper(II) carbonate + TX; chlorpyrifos + TX; coumafene + TX; chlorpyrifos + TX; caustic soda + TX; coumethoxystrobin + TX; chlorpyrifos + TX TX; Eugenol + TX; Cryolite + TX; Ladybug Monsieuron + TX;Fly attractant + TX; Thiazol + TX; Cuprous oxide (I) + TX; Benzoate + TX; Folic acid + TX; Cyazofamid + TX; Cyprodinium + TX; Cyprodinium + TX; Furazolidone + TX; Pyrethrum + TX; Trifluralin + TX; Codling moth GV + TX; Cyprodinium + TX; Cyclofenac + TX; Cyclofenac + TX; Diflubenzuron + TX; Cyfluthrin + TX; Trifluralin + TX; Acaricide + TX; Cymoxanil + TX; Cypermethrin + TX; Cypermethrin + TX; Cypermethrin + TX; Cyproconazole + TX; Cyproconazole + TX; Cyproconazole + TX; Cymoxanil + TX; Cymoxanil + TX; Cymoxanil + TX; Cymoxanil + TX; Cymoxanil + TX; Cymoxanil + TX; D-methrin + TX; Siberian valvular wasp + TX; DAEP + TX; Dazomet + TX; DCPM + TX; Imazalil + TX; Demethyl carbofuran + TX; Delcypermethrin + TX; Tebuconazole-O + TX; Tebuconazole-S + TX; Demeton-O + TX; Demeton-S + TX; Demeton-S-methyl + TX; Demeton-S-methyl sulfone + TX; Acaricide + TX; Chlorpyrifos + TX; Diazinon + TX; Dibutyl adipate + TX; Dibutyl phthalate + TX; Dibutyl succinate + TX; Isochlorpyrifos + TX; Dichlorophenoxyacetate + TX; Antibacterial + TX; Dichloronaphthoate + TX; 2,4-D propionic acid + TX; Dichlorvos + TX; Sclerotinia + TX; Diclofenac + TX; Pyridaben + TX; Chlornithiazine + TX; Trichlorfon + TX; Dioxin + TX; Phosphate + TX; Desnitron + TX TX; Dicyclopentadiene + TX; Ethylcarb + TX; DEET + TX; Dimethoate + TX; Difenoconazole + TX; Wild Bean Killer + TX; Thiamethoxam + TX; Flufenoxuron + TX; Diflubenzuron + TX; Flupyrimethanil + TX; Pea Leafminer Wasp + TX; Dimethoate + TX; Tetrafluorometholone + TX; Dimethoate + TX; Sclerotinia + TX; Thiamethoxam + TX; Mefenoxam + TX; Dimethoate + TX; Dimethoate + TX; Dimethoate + TX; Dimethyl Disulfide + TX; Dimethyl Phthalate + TX; Difenoconazole + TX; Difenoconazole + TX; Difenoconazole + TX; Difenoconazole + TX; Difenoconazole + TX; Difenoconazole + TX; Difenoconazole + TX; Difenoconazole + TX; Difenoconazole + TX; Difenoconazole + TX; Difenoconazole + TX; Difenoconazole + TX TX; fipronil + TX; benzyl ether + TX; phosmet + TX; diphenylamine + TX; pyrithione + TX; nonadecanedane + TX; disulfiram + TX; phorate + TX; phosmet + TX;Dithiazoline + TX; Thiamethoxam + TX; Dithiocarbamate + TX; Dodecano-8-en-1-ylacetate + TX; Dodecylmorpholine + TX; Dodecyl + TX; Doxorubicin + TX; Phenoxypropyricide + TX; Domipherex + TX; Dolactin + TX; Difenoconazole + TX; DSP + TX; Ecstatone + TX; Kefensan + TX; Emafenoxam Benzoate + TX; EMPC + TX; Dextromethorphan + TX; Encarsia formosa + TX; Endothioprine + TX; Herbadox + TX; Indomethacin + TX; Enoxacin + TX; Enrofloxacin + TX; Insect pathogenic bacteria + TX; Insect pathogenic fungi + TX; Insect pathogenic viruses + TX; EPBP + TX; Flutriafol + TX; Irinoctin + TX; Aphidida albicans + TX TX; Cypermethrin + TX; Ethiconazole + TX; Thiamethoxam + TX; Ethiocarb + TX; Ethiophanate + TX; Ethiophanate-methyl + TX; Ethiophanate + TX; Ethiophanate-methyl + TX; Ethyl methoxyquin + TX; Ethyl 4-methyloctanoate + TX; Ethyl formate + TX; Ethylhexane + TX; Ethylpyridinium + TX; Ethoxyfenozide + TX; Chlorpyrifos + TX; Ethylpyridinium + TX; Eugenol + TX; Eurax + TX; EXD + TX; Exo-Western pine bark beetle pheromone + TX; Oxafloxacin + TX; Valproic acid + TX; Farnesol and Nerolidol + TX; Fibentel + TX; Imidacloprid + TX; Enoxaflutole + TX; Benzyl + TX; Chlorpyrimethanil + TX; Quinalox + TX TX; Fenbendazole + TX; Cyproconazole + TX; Fenbutanil + TX; Quinoline + TX; Ethylcarbamide + TX; Pendiflubenzuron + TX; Mefenoxam + TX; Cyclocarb + TX; Fenitrothion + TX; Butyric acid + TX; Difenoconazole + TX; Benzocarb + TX; Oxypyrimamide + TX; Cyanobacterium + TX; Fenoxycarb + TX; Seed dressing + TX; Fenbenzan + TX; Pyralid + TX; Cypermethrin + TX; Cypermethrin + TX; Benzoyl + TX; Butazoline + TX; Amifenopterid + TX; Azoxystrobin + TX; Fenoxam + TX; Fenthion + TX; Ethyl Fenthion + TX; Triphenyltin + TX; Triphenyltin Acetate + TX; Triphenyltin Chloride + TX; Triphenyltin Hydroxide + TX; Cypermethrin + TX; Ferrous + TX; pyraclostrobin + TX; ferric phosphate + TX; fipronil + TX; flufenoxuron + TX; flonicamid + TX;Florfenicol + TX; Pyridaben + TX; Pyrimethanil + TX; Fluazinam + TX; Acetobacter + TX; Flubendazole + TX; Flufenoxuron + TX; Flufenoxuron + TX; Flufenoxuron + TX; Flufenoxuron + TX; Cypermethrin + TX; Fludioxonil + TX; Biflufenoxuron + TX; Pyrimethanil + TX; Flufenoxuron + TX; Flufenoxuron + TX; Flufenoxuron + TX; Trifluthrin + TX; Fluinbazide + TX; Fludioxonil + TX; Fludioxonil + TX; Flufenoxuron + TX; Flufenoxuron + TX; Flufenoxuron + TX; Flufenoxuron + TX; Flufenoxuron + TX; Flufenoxuron + TX; Flufenoxuron + TX; Flufenoxuron + TX; Flufenoxuron + TX; Flufenoxuron + TX; Flufenoxuron + TX; Flufenoxuron + TX; Flufenoxuron + TX TX; Sulfocarb + TX; Fluoxadiazon + TX; Fluopyram + TX; Tebuconazole + TX; Fluopyram + TX; Captan + TX; Dichlorvos + TX; Chlorpyrifos + TX; Formaldehyde + TX; Amitraz + TX; Amitraz Hydrochloride + TX; Ango + TX; Alfonium + TX; Fosetyl-aluminum + TX; Butazophos + TX; Thiazophos + TX; Butazophos + TX; Southern pine bark beetle pheromone + TX; Wheat bran + TX; Furazolidone + TX; Furazolidone + TX; Furazolidone + TX; Pyrethrum + TX; Furfural + TX; Gibberellin + TX; Glyphosate + TX; Lubricant Mixture I + TX; Lubricant Mixture II + TX; Lubricant Mixture III + TX; Luring agent IV + TX; Biguanidine triacetate + TX; Benzyl ether + TX; Chlorfenapyr + TX; Hexamethonium + TX; Heptenyl + TX; *Heterobacter oryzae* and *Heterobacter macrocarbazin* + TX; Hexaconazole + TX; Cetyl cyclopropanecarboxylate + TX; Flufenoxuron + TX; Hexenoxuron + TX; Thiamethoxam + TX; *Spotted ladybug* + TX; Cycloconazole (racemic-(1S,2S)-1-(4-chlorophenyl)-2-(1,2,4-triazol-1-yl)cycloheptanol) + TX; Flufenoxuron + TX; Quicklime (calcium hydroxide) + TX; Hymexazol + TX; Quinoline + TX; Icaridin + TX; Imanin (hypericin) + TX; imazalil + TX; imazalil sulfate + TX; imazalil + TX; imidacloprid + TX; biguanide octylamine + TX; indoxacarb + TX; indopyr + TX;Iodocarb + TX; Iprodione + TX; Ifentrifluconazole + TX; Isopropylquinoline + TX; Isoprothiolane (IBP) + TX; Iprodione + TX; Valproic acid + TX; Tetranythiocarbamate + TX; Tetranythiocarbamate + TX; IPSP + TX; Isamidophos + TX; Chlorpyrifos + TX; Methamidophos + TX; Iprodione + TX; Iprodione + TX; Transplanting agent + TX; Iprodione + TX; Isoprothiolane + TX; Pyrazothiocarbamate + TX; Iprodione + TX; Iprodione + TX; Isoxazol + TX; Ivermectin + TX; Scarab beetle pheromone + TX; Jasmine I + TX; Jasmine II + TX; Juvenile hormone I + TX; Juvenile hormone II + TX TX; Juvenile hormone III + TX; Thiamethoxam + TX; Kanamycin + TX; Kasugamycin + TX; Kasugamycin hydrochloride hydrate + TX; Kinetin + TX; Acetylpyridinium + TX; Azoxystrobin + TX; Bacillus thuringiensis subsp. Kustag + TX; λ-cyhalothrin + TX; Citrus citrus scale parasitic wasp + TX; Parafenoprolol + TX; Levamisole + TX; Trimethyldioxane + TX; Acetaminophen + TX; Pesticide for Spodoptera litura + TX; Clofenuron + TX; Chlorfenapyr + TX; Phosphate + TX; m-isopropylphenyl methylcarbamate + TX; Mirid bug + TX; Magnesium phosphide + TX; Malathion + TX; Maleic hydrazine + TX; Propiconazole + TX; Cabbage looper NPV + TX; Mancozeb + TX; Mancozeb + TX TX; Toluene-methyl + TX; Dimethomorph + TX; Mancozeb + TX; Azoxystrobin + TX; Mebendazole + TX; Phosphamidon + TX; Tetramethrin + TX; Acetylpyridinium + TX; Chlorfluazuron + TX; Megacodone + TX; Meloxiconazole + TX; Apimethoate + TX; Cyprodinil + TX; Dithiamethoxam + TX; Mepiquat chloride + TX; Chlorpyrifos + TX; Acaricide + TX; Fenoxacin + TX; Mefenoxam + TX; Metalaxyl + TX; Metalaxyl-M + TX; Methaldehyde + TX; Mefenoxam + TX; Mefenoxam-potassium + TX; Mefenoxam-sodium + TX; Yellow-stalked flea + TX; Metarhizium anisopliae (grasshopper variant) + TX; Metarhizium anisopliae (beetle variant) + TX; Methylpyridinium + TX; tebuconazole + TX; chlorfenapyr + TX; methamidophos + TX; sulfadiazine + TX; chlorpyrifos + TX; cypermethrin + TX; thiophanate-methyl + TX;Insecticidal phosphide + TX; Mefenoxam + TX; Acetaminophen + TX; Quinalazine + TX; Cypermethrin + TX; Methoxyfenozide + TX; Sterilicide + TX; Methyleugenol + TX; Iodomethacin + TX; Methylneodecanamide + TX; Mancozeb + TX; Methoxyfenozide + TX; Mefenoxam + TX; Phenoxybenzone + TX; Phenoxybenzone + TX; Tetracycline + TX; Mefenoxam + TX; Carbendazim + TX; MGK 264 + TX; Milbemycin + TX; Milbemoxim + TX; Phoxim + TX; Molentaxel Tartrate + TX; Sterilidine + TX; Moxifloxacin + TX; Insecticidal + TX; Acetaminophen + TX; Azoxystrobin + TX; Varicella spp. Combination + TX; N-[2-[2,4-dichloro-phenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide + TX; N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-[(2-isopropylphenyl)methyl]-1-methyl-pyrazole-4-carboxamide + TX; Sodium mancozeb + TX; Dibromophos + TX; NC-170 + TX; Namastem + TX; European New Pine Sawfly NPV and Red-headed New Pine Sawfly NPV + TX; Niclosamide-ethanolamine + TX; Nicotine + TX; Nicotine sulfate + TX; Nicotinamide + TX; Nitrazolium + TX; Chloridine + TX; Cypermethrin + TX; Phthalosporin + TX; Sodium thiosulfate + TX; Nornicotinamide + TX; Fluorouracil + TX; Polyfluorourea + TX; Fluoropyrimidine + TX TX; O,O,O',O'-Tetrapropyl dithiophosphate + TX; Octadecto-2,13-dien-1-yl acetate + TX; Octadecto-2,13-dien-1-yl acetate + TX; Octathiazoline + TX; Furazolidone + TX; Oleic acid + TX; Omethoate + TX; Heconazole + TX; Small-flowered bug species + TX; Oxime azoxystrobin + TX; Osthol + TX; Filachlor + TX; Oxystrobin + TX; Oxystrobin + TX; Oxystrobin + TX; Oxystrobin + TX; Oxystrobin + TX; Oxystrobin + TX; Oxystrobin + TX; Oxystrobin + TX; Oxystrobin + TX; Oxystrobin + TX; Oxystrobin + TX; Phosphite + TX; isofenphos + TX; sulfone + TX; oxytetracycline + TX; oxytetracycline dihydrate + TX; paclobutrazol + TX; *Paecilomyces roximate* + TX; paraoxon + TX; parathion + TX; methyl parathion + TX; parbendazole + TX;Isoprothiolane + TX; Tebuconazole + TX; Pendimethoate + TX; Pendimethoate + TX; Fluopyram + TX; Pyraclostrobin + TX; Permethrin + TX; Petroleum + TX; pH 60-38 + TX; Cyazofamid + TX; Indomethacin + TX; Phosphate + TX; Ratphos + TX; Phosphamidon + TX; Thiophanate + TX; Glyphosate + TX; Azoxystrobin + TX; Chlorpyrifos + TX; Phosphamidon + TX; Fipronil + TX; Phosphamidon + TX; Phosphamidon + TX; Phosphamidon + TX; Phosphamidon + TX; Phosphamidon + TX; Phosphamidon + TX; Phenylthion + TX; Phenylthion + TX; Phytosyl chlorpyrifos + TX; Tetraazolidinium + TX; Azoxystrobin + TX; Pimobendan + TX; Warfarin + TX; Piperaldehyde + TX; Piperyl Butyl ether + TX; Synergistic aldehyde + TX; Methamidophos + TX TX; Pirimicarb + TX; Methylpyrimidine + TX; Polycarbamate + TX; Naphthylmethrin + TX; Polyoxin B + TX; Polyoxin D + TX; Potassium Ethyl Xanthate + TX; Potassium Hydroxyquinoline Sulfate + TX; Praziquantel + TX; Precipitin I + TX; Precipitin II + TX; Precipitin III + TX; Aminopyrimidine + TX; Thiamethoxam + TX; Prochloraz + TX; Profenofos + TX; Profenofos + TX; Profenofos + TX; Cypermethrin + TX; Cyclophosphamide + TX; Cyclophosphamide + TX; Propiconazole + TX; Propine + TX; Propine + TX; Propine + TX; Propine + TX; Propine + TX; Propine + TX; Propine + TX; Propine + TX; Propine + TX; Propine + TX; Propine + TX; Propine + TX; Propine + TX; Propine + TX; Propine + TX; Propine + TX; Propine + TX TX; Ioquinazon + TX; Ethiazophos + TX; Prothioconazole + TX; Prothioconazole + TX; Fruiting + TX; Pyrethroid + TX; Fluopyram + TX; Pymetrozine + TX; Pyraclostrobin + TX; Pyraclostrobin + TX; Azoxystrobin + TX; Pyraclostrobin + TX; Pyraclostrobin + TX; Pyrethroid + TX; Pyrethroid + TX; Pyrethroid + TX; Pyrethroid + TX; Pyrethroid + TX; Pyrethroid I + TX; Pyrethroid II + TX; Pyrethroid (natural product) + TX; Pyrethroid (natural product) + TX; Pyraclostrobin + TX; Pyridaben + TX; Pyridaben + TX; Pyridaben + TX; Pyridaben + TX; Pyridaben + TX; Pyridine-4-amine + TX; pyridaben + TX; flufenoxuron + TX; pyrimethanil + TX; pyrimethanil + TX; pyraclostrobin + TX; benzoyl + TX;Piriprofen + TX; Pyriproxyfen + TX; Azoxystrobin + TX; Rhein + TX; Magnolia officinalis extract + TX; Quinalox + TX; Quinalox-methyl + TX; Alginate + TX; Quinoflavone + TX; Quinopyramine + TX; Quinothiazoline + TX; Quinoxaline + TX; Pentachloronitrobenzene + TX; R-1492 + TX; R-Methamphetamine + TX; Polygonum cuspidatum extract + TX; Ribavirin + TX; Rotenone + TX; Ranidin + TX; Veratrum saba + TX; Octapoxetine + TX; Onyx glycoside + TX; Cymoxanil + TX; Fluoxetine + TX; Silachlor + TX; Synergistic powder + TX; Sesamol + TX; Insect attractant + TX; Flusilazole + TX; Silthiamethoxam + TX; Silomethasone + TX; Silfluzol + TX; Sodium tetrathiocarbonate + TX; Threshion + TX; Sodium dimethoate + TX; Ethyl spinosad + TX; Spinosad + TX; Spirodiclofen + TX; Spirodiclofen + TX; Spirotetracycline + TX; Spirocyclohexane + TX; Caterpillar nematode + TX; Small leafroller nematode + TX; Noctuid moth nematode + TX; Grifola frondina + TX; Rhizoctonia solani + TX; Reissne nematode + TX; Mole cricket nematode + TX; Species of Nematodes + TX; Streptomycin + TX; Streptomycin sesquisulfate + TX; Fungicide + TX; Sulfodioxonium + TX; Sulfadiazine + TX; Sulfur + TX; Thiophanate + TX; Tar + TX; T-flumethoprim + TX; TCMTB + TX; TDE + TX; Tebuconazole + TX; Tebufenozide + TX; Pyridaben + TX; Isobutylethoxyquin + TX; Butylpyrimidine + TX; Tetrachloronitrobenzene + TX; Flufenoxuron + TX; Heptafluthrin + TX; Dithion + TX; Cypermethrin + TX; Terbuphos + TX; Terbuphos + TX; Insecticidal + TX; Flufenoxuron + TX; Tetradec-11-en-1-ylacetate + TX; Tetrachlorfenapyr + TX; Acephate + TX; Tetrafluthrin + TX; Acaricide + TX; Thiamethoxam + TX; Thiamethoxam + TX; Thiamethoxam + TX; Thiamethoxam + TX; Thiamethoxam + TX; Thiazinon + TX; Thiamethoxam + TX; Thiamethoxam + TX; Thifluzamide + TX; Insecticidal + TX; Insecticidal Cyclocarboxylic Acid + TX; Insecticidal Cyclocarboxylic Acid Oxychloride + TX; Thiamethoxam + TX; Dimethoate + TX; Methyl phorate + TX; Thiophanate + TX; Methyl thiophanate + TX; Acaricide + TX; Carbohydrate + TX; Carbohydrate-disodium + TX;Thiram + TX; Bacillus thuringiensis + TX; Thiamethoxam + TX; Tiamulin + TX; Tioxymid + TX; Methyl thiophanate + TX; Azoxystrobin + TX; Trifluthrin + TX; Paraben + TX; Tetrabromopropylate + TX; Permethrin + TX; Tratamide + TX; Triadimefon + TX; Triadimefon + TX; Triazophos + TX; Azoxystrobin + TX; Triazophos + TX; Imidacloprid + TX; Defoliant + TX; Trichlorfon + TX; Isofenphos-3 + TX; Phosphorus + TX; Trichogramma + TX; Trichloroisocyanuric acid + TX; Trichlorfon + TX; Triamcinolone + TX; Azoxystrobin + TX; Fluopyram + TX; Lactobacillus + TX; TX; Azoxystrobin + TX; Mediterranean fruit fly attractant + TX; Mediterranean fruit fly attractant A + TX; Mediterranean fruit fly attractant B1 + TX; Mediterranean fruit fly attractant B2 + TX; Mediterranean fruit fly attractant C + TX; Mixed carbendazim + TX; Trichloroisocyanuric acid + TX; Anti-rot ester + TX; Anti-rot ester-ethyl + TX; Tebufenozide + TX; Mefenoxam + TX; Chuangke + TX; Torrafenib + TX; Western blind mite + TX; Uniconazole + TX; Urethroid + TX; Validamycin + TX; Valhalax + TX; Aphid + TX; Mefenoxam + TX; Veratrine + TX; Veratrine + TX; Synergistic alkyne + TX; Verticillium spp. + TX; Ethylene + TX; XMC + TX; Xylenol + TX; Zeatin + TX; ζ-Cypermethrin + TX; kasugamycin + TX; zinc naphthenate + TX; zinc thiamethoxam + TX; zineb + ​​TX; zinc thiram + TX; pyraclostrobin + TX; benzymamide + TX; 2-(difluoromethyl)-N-[(3S)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (this compound can be prepared by the method described in WO 2014 / 095675) + TX; methyl 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1,2,4-triazol-1-ylmethyl)cyclopentanecarboxylate (this compound can be prepared by the method described in WO2019 / 093522) + TX; (2R)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propionate methyl ester (this compound can be prepared by the method described in WO 2019 / 093522) + TX;5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)cyclopropyl]pyrimidin-2-amine (this compound can be prepared by the method described in WO 2021 / 255093) + TX; aminolpyridine (this compound can be prepared by the method described in WO2014 / 006945) + TX; thiamethoxam (this compound can be prepared by the method described in WO 2011 / 138281) + TX; 1-[6-(difluoromethyl)-5-methyl-3-pyridyl]-4,4-difluoro-3,3-dimethyl-isoquinoline (this compound can be prepared by the method described in WO 2017 / 016915) + TX; 1-[4-(difluoromethoxy)-2-methyl-phenyl]-2-(1,2,4-triazol-1-yl)-1-[1-(trifluoromethyl)cyclopropyl]ethanol (This compound can be prepared by the method described in WO 2021 / 249800) + TX; 1-[2-chloro-4-(difluoromethoxy)phenyl]-2-(1,2,4-triazol-1-yl)-1-[1-(trifluoromethyl)cyclopropyl]ethanol (This compound can be prepared by the method described in WO 2021 / 249800) + TX; 1-(5,6-dimethyl-3-pyridyl)-4,4-difluoro-3,3-dimethyl-isoquinoline (This compound can be prepared by the method described in WO 2017 / 016915) + TX; N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzylthiocarboxamide (this compound can be prepared by the method described in WO 2015 / 185485) + TX; 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide (this compound can be prepared by the method described in WO 2017 / 178245) + TX; fluopyram + TX; N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide (this compound can be prepared by the method described in WO 2015 / 185485) + TX; (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide (this compound can be prepared by the method described in WO 2018 / 153707) + TX; (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide (this compound can be prepared by the method described in WO 2013 / 092224) + TX;(2E)-2-methoxyimino-2-[3-methyl-2-[[(E)-1-[4-(trifluoromethyl)-2-pyridyl]ethyleneamino]oxymethyl]phenyl]methyl acetate (this compound can be prepared by the method described in WO 2022 / 033906) + TX; (2E)-2-methoxyimino-N-methyl-2-[3-methyl-2-[[(E)-1-[4-(trifluoromethyl)-2-pyridyl]ethyleneamino]oxymethyl]phenyl]acetamide (this compound can be prepared by the method described in WO 2022 / 033906) + TX; (2E)-2-[2-[[(E)-[3-(4-fluorophenyl)-1-methyl-prop-2-ynylene]amino]oxymethyl]-3-methyl-phenyl]-2-methoxyimino-N-methyl-acetamide (this compound can be prepared by WO 2022 / 033906) + TX; (2E)-2-[2-[[(E)-[3-(4-fluorophenyl)-1-methyl-prop-2-ynylene]amino]oxymethyl]-3-methyl-phenyl]-2-methoxyimino-N-methyl-acetamide (this compound can be prepared by WO 2022 / 033906) + TX; (Prepared by the method described in WO 2021 / 249928) + TX; (2E)-2-[2-[[(E)-[3-(4-fluorophenyl)-1-methyl-prop-2-ynyne]amino]oxymethyl]-3-methyl-phenyl]-2-methoxyimino-acetic acid methyl ester (This compound can be prepared by the method described in WO 2021 / 249928) + TX; 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-propyl]imidazolium-4-carboxylonitrile (This compound can be prepared by the method described in WO 2016 / 156290) + TX; 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxy-propyl]imidazolium-4-carboxylonitrile (This compound can be prepared by the method described in WO 2016 / 156290) + TX; 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)prop-2-ol (this compound can be prepared by the method described in WO 2017 / 029179) + TX; 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)prop-2-ol (this compound can be prepared by the method described in WO 2017 / 029179) + TX; 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)ethyl]pyrimidin-2-amine (this compound can be prepared by the method described in WO 2021 / 255093) + TX; 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(3,5-difluorophenyl)ethyl]pyrimidin-2-amine (this compound can be prepared by the method described in WO 2021 / 255093) + TX;N-[1-(2-fluorophenyl)cyclopropyl]-5-[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]pyrimidin-2-amine (this compound can be prepared by the method described in WO 2021 / 255093) + TX; 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)ethyl]pyrimidin-2-amine (this compound can be prepared by the method described in WO 2021 / 255093) + TX; 2-(difluoromethyl)-5-[2-[1-(2,6-difluorophenyl)cyclopropoxy]pyrimidin-5-yl]-1,3,4-oxadiazole (this compound can be prepared by the method described in WO 2021 / 255093) + TX; 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)cyclopropyl]pyrimidin-2-amine (This compound can be prepared by the method described in WO 2021 / 255093) + TX; 5-[(4-bromo-2-methyl-phenyl)methyl]-3-[3-(3-chloro-2-fluoro-phenoxy)-6-methyl-pyridazin-4-yl]-5,6-dihydro-4H-1,2,4-oxadiazine (This compound can be prepared by the method described in WO2021 / 255070) + TX; 3-[3-(3-cyclopropyl-2-fluoro-phenoxy)-6-methyl-pyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine (This compound can be prepared by the method described in WO 2021 / 255093) (Prepared by the method described in WO 2021 / 255070) + TX; N-(2,2,2-trifluoroethyl)-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]oxazol-4-carboxamide (This compound can be prepared by the method described in WO 2022 / 133114) + TX; 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenoxy]methyl]pyrazole-4-carboxylic acid ethyl ester (This compound can be prepared by the method described in WO 2022 / 133114) + TX; 1-[[4-[(Z)-2-ethoxy-3,3,3-trifluoro-prop-1-enoxy]phenyl]methyl]pyrazole-4-carboxylic acid ethyl ester (This compound can be prepared by WO 2022 / 133114) + TX; 1-[[4-[(Z)-2-ethoxy-3,3,3-trifluoro-prop-1-enoxy]phenyl]methyl]pyrazole-4-carboxylic acid ethyl ester (This compound can be prepared by WO 2022 / 133114) + TX; (Prepared by the methods described in WO 2020 / 056090 and WO 2021 / 183707) + TX; 1-[[4-[[2-(trifluoromethyl)-1,3-dioxolane-2-yl]methoxy]phenyl]methyl]pyrazole-4-carboxylic acid ethyl ester (This compound can be prepared by the methods described in WO 2020 / 056090 and WO 2021 / 183707) + TX;Methyl N-[[5-[4-(2,4-dimethylphenyl)triazol-2-yl]-2-methyl-phenyl]methyl]carbamate (this compound can be prepared by the method described in WO 2020 / 097012) + TX; 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 WO 2020 / 097012) + TX; Methyl N-[[5-[1-(4-cyclopropyl-2,6-difluoro-phenyl)pyrazol-3-yl]-2-methyl-phenyl]methyl]carbamate (this compound can be prepared by the method described in WO 2020 / 097012) + TX; TX; methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propionate (this compound can be prepared by the method described in WO 2019 / 093522) + TX; 4,4,5-trifluoro-3,3-dimethyl-1-(3-quinolinyl)isoquinoline + TX; 5-fluoro-3,3,4,4-tetramethyl-1-(3-quinolinyl)isoquinoline + TX; 2-methoxy-N-[methoxy-[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]acetamide (this compound can be prepared by the method described in WO2020 / 256113) + TX; N-[methoxy-[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]-2-methyl-propionamide (this compound can be prepared by the method described in WO 2020 / 256113) + TX; N-[methoxy-[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]butyramide (this compound can be prepared by the method described in WO 2020 / 256113) + TX; 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (this compound can be prepared by the method described in WO 2014 / 095675) + TX; 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide (this compound can be prepared by the method described in WO 2014 / 095675) + TX; 2-(difluoromethyl)-N-(1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide + TX;(5R)-3-[3-(3-chloro-2-fluoro-phenoxy)-6-methyl-pyridazin-4-yl]-5-[(2-chloro-4-methyl-phenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine (this compound can be prepared by the methods described in WO 2020 / 127780 and WO 2021 / 255070) + TX; (5S)-3-[3-(3-chloro-2-fluoro-phenoxy)-6-methyl-pyridazin-4-yl]-5-[(2-chloro-4-methyl-phenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine (this compound can be prepared by the methods described in WO 2020 / 127780 and WO 2021 / 255070) + TX; 3-[3-(3-chloro-2-fluoro-phenoxy)-6-methyl-pyridazin-4-yl]-5-[(2-chloro-4-methyl-phenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine (this compound can be prepared by the methods described in WO 2020 / 127780, WO 2021 / 255070) + TX; (Z)-3-methoxy-2-(2-methyl-5-phenyl-phenoxy)prop-2-enoic acid methyl ester (this compound can be prepared by the methods described in JP 2023078251) + TX; 2-[(2,6-difluoro-4-pyridinyl)-(2-methylpropionyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazol-4-carboxamide + TX; or its (R) or (S) enantiomers or mixtures + TX (this compound can be prepared by the methods described in WO 2017207362 A1, WO 2019105933 A1, WO 2020109511 A1, WO 2021244952 A1); 2-[(2,6-difluoro-4-pyridinyl)-(tetrahydropyran-4-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazolyl-4-carboxamide + TX; or its (R) or (S) enantiomers or mixtures thereof + TX (this compound can be prepared by the methods described in WO 2017207362 A1, WO 2019105933 A1, WO 2020109511 A1, WO 2021244952 A1). Prepared by the method described in A1); 2-[cyano-(2,6-difluoro-4-pyridinyl)amino]-5-methyl-N-spiro[3,4]octane-3-yl-thiazolyl-4-carboxamide + TX; or its (R) or (S) enantiomers or mixtures + TX (this compound can be prepared by the method described in WO 2017207362 A1, WO2019105933 A1, WO 2020109509 A1);2-[cyano-(2,6-difluoro-4-pyridinyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazol-4-carboxamide + TX; or its (R) or (S) enantiomers or mixtures + TX (this compound can be prepared by the methods described in WO 2017207362 A1, WO 2019105933 A1, WO 2020109509 A1); 2-[(2,6-difluoro-4-pyridinyl)-(2-methoxyacet ... Prepared by the methods described in WO 2020109511 A1, WO 2021244952 A1); 2-[acetyl-(2,6-difluoro-4-pyridyl)amino]-5-methyl-N-spiro[3,4]octane-3-yl-thiazolyl-4-carboxamide + TX; or its (R) or (S) enantiomers or mixtures + TX (this compound can be prepared by the methods described in WO2017207362 A1, WO 2019105933 A1, WO 2020109511 A1, WO 2021244952 A1); N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide (this compound can be prepared by the methods described in WO 2017 / 055473) + TX; N-[(1R)-1-benzyl-1,3-dimethylbutyl]-8-fluoroquinoline-3-carboxamide (this compound can be prepared by the method described in WO 2017 / 153380) + TX; N-[(1S)-1-benzyl-1,3-dimethylbutyl]-8-fluoroquinoline-3-carboxamide (this compound can be prepared by the method described in WO 2017 / 153380) + TX; 2-[(2,6-difluoro-4-pyridyl)-(oxetane-3-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazol-4-carboxamide + TX; or its (R) or (S) enantiomers or mixtures + TX (this compound can be prepared by the method described in WO 2017207362 A1, WO 2019105933 A1, WO Prepared by the method described in 2020109511 A1 and WO2021244952 A1); 2-[acetyl-(2,6-difluoro-4-pyridyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazolyl-4-carboxamide + TX;Or its (R) or (S) enantiomers or mixtures + TX (this compound can be prepared by the methods described in WO 2017207362 A1, WO 2019105933 A1, WO 2020109511 A1, WO 2021244952 A1); N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide + TX; or its (R) or (S) enantiomers or mixtures + TX (this compound can be prepared by the methods described in WO 2017 / 055473).

[0183] Further disclosure is made of two-component mixture compositions, wherein the term "TX1" represents compound (E)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester: a composition selected from the group consisting of: (4E,10Z)-tetradec-4,10-dienyl acetate + TX1; (7E,9Z)-dodec-7,9-dien-1-yl acetate + TX1; (E)-6-methylhept-2-en-4-ol + TX1; (E)-dec-5-en-1-yl acetate and (E)-dec-5-en-1-ol + TX1; (E)-tetrate-4-en-1-yl acetate + TX1; (S)-bioallethrin + TX1; (Z)-dodec-7-en-1-yl acetate + TX1; (Z)-hexadec-11-en-1-yl acetate + TX1; (Z)-Hexadec-11-enal + TX1; (Z)-Hexadec-13-en-11-yn-1-yl acetate + TX1; (Z)-Eicosate-13-en-10-one + TX1; (Z)-Tetradec-7-en-1-al + TX1; (Z)-Tetradec-9-en-1-ol + TX1; (Z)-Tetradec-9-en-1-yl acetate + TX1; 1,1-bis(4-chlorophenyl)-2-ethoxyethanol + TX1; 1-(2-chlorophenyl)-3,3-dimethyl-2-(1,2,4-triazol-1-ylmethyl)but-2-ol + TX1; 1-(5-bromo-2-pyridyl)-2-(2,4-difluorophenyl)-1,1-difluoro-3-(1,2,4-triazol-1-yl)prop-2-ol + TX1; 1-hydroxy-1H-pyridin-2-thione + TX1; 1-methylcyclopropene + TX1; 1-naphthylacetamide + TX1; 1-naphthylacetic acid + TX1; 2,2-dichlorovinyl-2-ethylsulfinylethylmethyl phosphate + TX1; 2,4-D + TX1; 2,4-DB + TX1; 2,6-dichloro-N-(4-trifluoromethylbenzyl)benzamide + TX1; 2-(1,3-dithiopentane-2-yl)phenyldimethylcarbamate + TX1; 2-(2-butoxyethoxy)ethyl piperate + TX1; 2-(4,5-dimethyl-1,3-dioxolane-2-yl)phenylmethylcarbamate + TX1; 2-(difluoromethyl)-N-((3R)-1,1,3-trimethylindane-4-yl)pyridine-3-carboxamide + TX1; 2-(octylthio)-ethanol + TX1; 2-bromo-2-bromomethyl-glutaronitrile + TX1; 2-chlorovinyl diethyl phosphate + TX1; 2-imidazolium ketone + TX1; 2-methyl(prop-2-ynyl)aminophenylmethylcarbamate + TX1; 2-cyanothioethyl laurate + TX1;3-(4-Chlorophenyl)-5-methylrhodanine + TX1; 3-(difluoromethyl)-1-methyl-N-[1,1,3-trimethylindan-4-yl]pyrazole-4-carboxamide + TX1; 3-(difluoromethyl)-N-(7-fluoro-1,1,3,3-tetramethyl-indan-4-yl)-1-methyl-pyrazole-4-carboxamide + TX1; 3-(difluoromethyl)-N-(7-fluoro-1,1,3,3-tetramethyl-indan-4-yl)-1-methyl-pyrazole-4-carboxamide + TX1; 3-chloro-6-methyl-5-phenyl-4-(2,4,6-trifluorophenyl)pyridazine + TX1; 3-methyl-1-phenylpyrazole-5-yldimethylcarbamate + TX1; 3-phenylphenol + TX1; 4,5-Dichlorodithiol-3-one + TX1; 4-(2,6-difluorophenyl)-6-methyl-5-phenyl-pyridazin-3-carboxylonitrile + TX1; 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-2,5-dimethyl-pyrazol-3-amine + TX1; 4-(quinoxaloline-2-ylamino)benzenesulfonamide + TX1; 4-[[6-[2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(1,2,4-triazol-1-yl)propyl]-3-pyridinyl]oxy]benzonitrile + TX1; 4-chloro-2-(2-chloro-2-methyl-propyl)-5-[(6-iodo-3-pyridinyl)methoxy]pyridazin-3-one + TX1; 4-CPA + TX1; 4-Methyl(prop-2-ynyl)amino-3,5-dimethylmethylcarbamate + TX1; 4-Methylnon-5-ol and 4-methylnon-5-one + TX1; 4-Phenylenol + TX1; 5-(1,3-benzodioxane-5-yl)-3-hexylcyclohex-2-enone + TX1; 5-amino-1,3,4-thiadiazol-2-thiol + TX1; 5-fluoro-2-(p-tolylmethoxy)pyrimidin-4-amine + TX1; 5-hydroxy-6-methyl-4-(((E)-pyridin-3-ylmethylene)amino)-4,5-dihydro-1,2,4-triazine-3(2H)-one + TX1; 5-methyl-6-thio-1,3,5-thiadiazine-3-ylacetic acid + TX1; 8-hydroxyquinoline sulfate + TX1; 11-Ethyl-10,12-dioxo-2,5,8-trithia-4,11-diazatricyclo[7.3.0.03,7]dodec-1(9),3,6-trien-6-carboxynitrile + TX1; 14-Methyloctadec-1-ene + TX1; [(9Z,11E)-tetradec-9,11-dienyl]acetate + TX1; [(Z)-dodec-9-enyl]acetate + TX1; abamectin + TX1; acephate + TX1; miticide + TX1; acetamiprid + TX1;Aspergillus + TX1; Acetaminophen + TX1; Aranamycin + TX1; Aranamycin-S-methyl + TX1; Flufenoxuron + TX1; Cotton Brown Leaf Roller GV + TX1; Agrobacterium radiata + TX1; Cotton Bollworm + TX1; Albendazole + TX1; Aldicarb + TX1; Propyrethroid + TX1; Aloxam + TX1; Allyl alcohol + TX1; Dichlorvos + TX1; α-Decidulin + TX1; α-Polycarb + TX1; Amblyoxadixyl Species + TX1; Azoxystrobin + TX1; Aspergillus + TX1; Sulfamethoxam + TX1; Fenmethoxam + TX1; Dichlorvos + TX1; Indoxam + TX1; Ammonium phosphate + TX1; Ammonium phosphate oxalate + TX1; Amitraz + TX1; Neonicotinic Acid + TX1; Celery cutworm NPV + TX1; *Protoceratops chinensis* + TX1; Pyrimidine + TX1; Dimethoate + TX1; Fluphenyladenine + TX1; Anthraquinone + TX1; Antoxin + TX1; Short-spur aphid wasp + TX1; Cotton aphid parasitic wasp + TX1; Aphid gall midge + TX1; Ethyl chlorpyrifos + TX1; Aureobasidium aureum + TX1; Alfalfa silver-striped cutworm NPV + TX1; Abamectin B1a + TX1; Azaconazole + TX1; Azadirachtin A + TX1; Pyrazosulfan + TX1; Methylpyridinium + TX1; Ethyl glutathione + TX1; Methyl glutathione + TX1; Fenmethoxam + TX1; Azoxystrobin + TX1; Bacillus spheroides (Ned) + TX1; Bacillus thuringiensis + TX1; Bacillus thuringiensis δ-endotoxin + TX1; Bacillus thuringiensis subsp. *subsalicylate* + TX1; Baculovirus + TX1; Pyrethroid + TX1; Beauveria bassiana + TX1; Benzophenone + TX1; Benzophenone-M + TX1; Benazepril + TX1; Benzyl + TX1; Carbofuran + TX1; Benomyl + TX1; Sulfuric acid + TX1; Benzethirimol + TX1; Benzalkonium chloride + TX1; Phytoprofen + TX1; Benzethirimol + TX1; Benzofenazate + TX1; Benzac-methyl + TX1; β-Cypermethrin + TX1; β-Cypermethrin + TX1; Benzoxazin + TX1; Bifenazate + TX1; Bifenthrin + TX1; Acaricide + TX1; Bioallyl + TX1; Biocypermethrin + TX1; Biopermethrin + TX1 TX1; Biobenzylfuran + TX1; Diflubenzuron + TX1; Diflubenzuron + TX1; Bifenazate + TX1; Bifenazate + TX1; Isopyram + TX1; Borax + TX1; Bordeaux mixture + TX1;Cyclomethrin + TX1; Bromophos + TX1; Bromocypermethrin + TX1; Bromodiflubenzuron + TX1; Bromophenylenephos + TX1; Bromothion + TX1; Bromothion-ethyl + TX1; Fenoxacillin + TX1; Dimethoate + TX1; Ethylpyrimethanil + TX1; Thiazide + TX1; Buserelin + TX1; Busulfan + TX1; N-[6-[[(Z)-[(1-methyltetrazole-5-yl)-phenyl-methylene]amino]oxymethyl]-2-pyridyl]carbamate butyl-3-yneylylene + TX1; Carbofuran + TX1; Terfenoxam + TX1; Butanone + TX1; Butyl ester + TX1; DEET + TX1; Butoxy(polypropylene glycol) + TX1; Butanone sulfonate + TX1; Butylamine + TX1; Thiophanate + TX1; Calcium alcohol + TX1; Calcium phosphate + TX1; Calcium polysulfide + TX1; Canbendazole + TX1; Captan + TX1; Carbendazim + TX1; Carbaryl + TX1; Carbendazim hydrochloride + TX1; Carbofuran + TX1; Thiophanate + TX1; Carbofuran + TX1; Carbofuran + TX1; Carbofuran + TX1; Carbofuran + TX1; Cyproconazole + TX1; Pyralid + TX1; Pyralid hydrochloride + TX1; Cephalexin + TX1; Cefotaxime + TX1; Cefoquinol + TX1; Ceftiofur + TX1; Cystec + TX1; Servadine + TX1; Acaricide + TX1; Chitosan + TX1; Chlorpheniramine + TX1; Chloralose + TX1; Chlorantraniliprole + TX1; Acaricide + TX1; Amitraz + TX1; Ethephon + TX1; Phosphorus oxychloride + TX1; Brofenoxam + TX1; Chlorfenapyr + TX1; Tetramethrin + TX1; Clofenthion + TX1; Difenoconazole + TX1; Chlormethoate + TX1; Chlormequat + TX1; Chlormequat + TX1; Amitraz + TX1; Difenoconazole + TX1; Dimethoate + TX1; Chlorothalonil + TX1; Chlorpyrifos + TX1; Chlorpyrifos + TX1; Chlorpyrifos-methyl + TX1; Chlortetracycline + TX1; Chlormethoate + TX1; Ethiophanate-methyl + TX1; Cholecalciferol + TX1; Cyclofenac + TX1; Common lacewing + TX1; Cucurbitacin + TX1; Cucurbitacin I + TX1; Cucurbitacin II + TX1; cis-jasmone + TX1; cis-resmethrin + TX1; cismethrin + TX1; Clenbuterol + TX1;Ganbaosu + TX1; Dichlorvos + TX1; Benzimidazine + TX1; Clostridium + TX1; Thiamethoxam + TX1; Chlorpyrifos (acetamide) + TX1; Dodecadienol + TX1; Copper acetate + TX1; Copper hydroxide + TX1; Copper naphthenate + TX1; Copper octanoate + TX1; Copper oleate + TX1; Copper oxide + TX1; Copper oxychloride + TX1; Copper silicate + TX1; Copper sulfate + TX1; Copper(II) carbonate + TX1; Chlorpyrifos + TX1; Coumarin + TX1; Coumarin + TX1; Coumarin + TX1; Coumarin + TX1; Coumarin + TX1; Coumarin + TX1; Coumarin + TX1; Cryolite + TX1; Crassula ovata + TX1; Fly attractant + TX1; Thiazol + TX1; Cuprous oxide (I) + TX1; Benzoate + TX1; Folic acid + TX1; Cyazofamid + TX1; Cyprodinium + TX1; Furazolidone + TX1; Pyrethrum + TX1; Triflupyridamole + TX1; Codling moth GV + TX1; Cyprodinium + TX1; Cyfluthrin + TX1; Diflubenzuron + TX1; Cypermethrin + TX1; Trifluthrin + TX1; Acaricide + TX1; Cymoxanil + TX1; Cypermethrin + TX1; Cypermethrin + TX1; Cyproconazole + TX1; Azoxystrobin + TX1; Cyproconazole + TX1; Cymoxanil + TX1; Cymoxanil + TX1; Cymoxanil + TX1; Cymoxanil + TX1; Cymoxanil + TX1; D-methoxyfenozide + TX1; Siberian parasitic wasp + TX1; DAEP + TX1; Dazomet + TX1; DCPM + TX1; Imazalil + TX1; Demethylcarbofuran + TX1; Delcypermethrin + TX1; Tebufenozide-O + TX1; Tebufenozide-S + TX1; Demeton-O + TX1; Demeton-S + TX1; Demeton-S-methyl + TX1; Demeton-S-methylsulfone + TX1; Acaricide + TX1; Chlorpyrifos + TX1; Diazinon + TX1; Dibutyl adipate + TX1; Dibutyl phthalate + TX1; Dibutyl succinate + TX1; Isochlorpyrifos + TX1; Dichlorophenoxyacetate + TX1; Bactericide + TX1; Dichloronaphthoate + TX1; 2,4-D propionic acid + TX1; Dichlorvos + TX1; Sclerotinia + TX1; Dichloroisocyanurate + TX1; Pyridaben + TX1; chlornitramine + TX1; trichlorfon + TX1; dichlorvos + TX1; chlorpyrifos + TX1; desinol + TX1; dicyclopentadiene + TX1;Ethylcarbamide + TX1; DEET + TX1; Dimethoate + TX1; Difenoconazole + TX1; Wild Bean Killer + TX1; Thiamethoxam + TX1; Flufenoxuron + TX1; Diflubenzuron + TX1; Flupyridamole + TX1; Pea Leafminer Fly Azoxystrobin + TX1; Dimethoate + TX1; Tebufenozide + TX1; Dimethoate + TX1; Imidacloprid + TX1; Thiamethoxam + TX1; Mefenoxam + TX1; Dimethoate + TX1; Dimethoate + TX1; Dimethoate + TX1; Dimethyl Disulfide + TX1; Dimethyl Phthalate + TX1; Difenoconazole + TX1; Difenoconazole + TX1; Difenoconazole + TX1; Difenoconazole + TX1; Difenoconazole + TX1; Difenoconazole + TX1; Difenoconazole + TX1; Difenoconazole + TX1 TX1; lindimethalin + TX1; dichlorvos + TX1; fipronil + TX1; benzyl ether + TX1; phosmet + TX1; diphenylamine + TX1; pyrithione + TX1; nonadecanedane + TX1; disulfiram + TX1; phorate + TX1; phosmet + TX1; dithiocarbamate + TX1; thiamethoxam + TX1; dodecano-8-en-1-ylacetate + TX1; dodecylmorpholine + TX1; doxycycline + TX1; doxycycline + TX1; doxycycline + TX1; fenoxypropynt + TX1; domipherex + TX1; doxorubicin + TX1; doxycycline + TX1; DSP + TX1; ecdysterone + TX1; chlorpyrifos + TX1; emamectin benzoate + TX1; EMPC + TX1; dextromethorphan + TX1; Encarsia formosa + TX1; Endothiocyanate + TX1; Glufosinate + TX1; Indomethacin + TX1; Enoxacin + TX1; Enrofloxacin + TX1; Insect pathogenic bacteria + TX1; Insect pathogenic fungi + TX1; Insect pathogenic viruses + TX1; EPBP + TX1; Flutriafol + TX1; Irinoctazol + TX1; Aphids + TX1; Cypermethrin + TX1; Ethioconazole + TX1; Thiamethoxam + TX1; Ethiocarb + TX1; Ethiophos + TX1; Ethiophanate-methyl + TX1; Ethiophanate + TX1; Ethiophanate-methyl + TX1; Ethyl formate + TX1; Ethylhexane + TX1; Ethylhexanediol + TX1; Permethrin + TX1; etoxazole + TX1; chlorpyrifos + TX1; ethirimol + TX1; eugenol + TX1; eugenol + TX1; EXD + TX1; exo-Western pine bark beetle collection pheromone + TX1;Oxadiazon + TX1; Valproate + TX1; Farnesol and Nerolidol + TX1; Fibentel + TX1; Imidacloprid + TX1; Enoxaflutole + TX1; Benzophos + TX1; Chlorpyrifos + TX1; Quinalox + TX1; Fenbendazole + TX1; Cyproconazole + TX1; Fenbutanil + TX1; Quinoline + TX1; Ethylcarbamide + TX1; Pyrimethanil + TX1; Mefenoxam + TX1; Cyclopyralid + TX1; Fenitrothion + TX1; Butoxam + TX1; Difenoconazole + TX1; Benthiocarb + TX1; Oxypyrimethanil + TX1; Cyazofamid + TX1; Fenoxycarb + TX1; Pyrimethanil + TX1; Cypermethrin + TX1 TX1; Benzyl sulfide + TX1; Butadienemorph + TX1; Amifenozide + TX1; Azoxystrobin + TX1; Fonsodium + TX1; Fenthion + TX1; Ethyl Fonsodium + TX1; Triphenyltin + TX1; Triphenyltin Acetate + TX1; Triphenyltin Chloride + TX1; Triphenyltin Hydroxide + TX1; Cypermethrin + TX1; Ferrous Fram + TX1; Azoxystrobin + TX1; Ferric Phosphate + TX1; Fipronil + TX1; Flufenoxuron + TX1; Flufenoxuron + TX1; Florfenicol + TX1; Pyridaben + TX1; Pyrimethanil + TX1; Fluazinam + TX1; Acetobacter + TX1; Flufenadil + TX1; Flufenoxuron + TX1; Flufenoxuron + TX1 TX1; Flufenoxuron + TX1; Cypermethrin + TX1; Fludioxonil + TX1; Bifenazate + TX1; Pyrimethanil + TX1; Flufenoxuron + TX1; Flufenoxuron + TX1; Trifluthrin + TX1; Fluinbazin + TX1; Fludioxonil + TX1; Flusulfanilamide + TX1; Fluopyram + TX1; Fluopyram + TX1; Fluopyram + TX1; Fluopyram + TX1; Fluopyram + TX1; Fluopyram + TX1; Fluopyram + TX1; Fluopyram + TX1; Fluopyram + TX1; Fluopyram + TX1; Fluopyram + TX1; Fluopyram + TX1; Fluopyram + TX1; Captan + TX1; phosmet + TX1; chlorpyrifos + TX1; formaldehyde + TX1; chlorfenapyr + TX1; chlorfenapyr hydrochloride + TX1; fenpropathrin + TX1; acaricide + TX1; fosetyl-aluminum + TX1;Phosphine + TX1; Thiazol + TX1; Butylthion + TX1; Southern pine bark beetle collection pheromone + TX1; Wheat bran + TX1; Furazolidone + TX1; Furazolidone + TX1; Furazolidone + TX1; Pyrethrum + TX1; Furfural + TX1; Gibberellin + TX1; Glyphosate + TX1; Enthalpyr mixture I + TX1; Enthalpyr mixture II + TX1; Enthalpyr mixture III + TX1; Enthalpyr mixture IV + TX1; Biguanidin triacetate + TX1; Benzyl ether + TX1; Chlorfenapyr + TX1; Hexamethonium + TX1; Hepten + TX1; *Heterobacter oryzae* and *Heterobacter macrocarpa* + TX1; Hexaconazole + TX1; Cetyl cyclopropanecarboxylate + TX1; Flufenoxuron + TX1; Hexotropic attractant + TX1; Hexourea + TX1; Thiamethoxam + TX1; Ladybug + TX1; Cycloconazole (racemic-(1S,2S)-1-(4-chlorophenyl)-2-(1,2,4-triazol-1-yl)cycloheptanol) + TX1; Fluroxypyr + TX1; Quicklime (calcium hydroxide) + TX1; Hymexazol + TX1; Quinoline + TX1; Icaridin + TX1; Hypericin + TX1; Imazalil + TX1; Imazalil sulfate + TX1; Imidacloprid + TX1; Imidacloprid + TX1; Biguanide octylamine + TX1; Indoxacarb + TX1; Indopyram + TX1; Iodopropynyl butyl methyl ester + TX1; Smectin + TX1; Ifentrifluconazole + TX1; Isopropylquinoline + TX1; Isoprothiolane (IBP) + TX1; Iprodione + TX1; Valproic acid + TX1; Tetranythiocarbamate + TX1; Tetranythiocarbamate + TX1; IPSP + TX1; Isamidophos + TX1; Chlorpyrifos + TX1; Methamidophos + TX1; Isopropylthiocarbamate + TX1; Isopropylfluopyram + TX1; Transplanting agent + TX1; Isopropylcarbamate + TX1; Isoprothiolane + TX1; Pyraclostrobin + TX1; Isopropylthiocarbamate + TX1; Isopropylthiocarbamate + TX1; Isoxazol + TX1; Ivermectin + TX1; Scarab beetle pheromone + TX1; Jasmine I + TX1; Jasmine II + TX1; Juvenile hormone I + TX1; Juvenile hormone II + TX1; Juvenile hormone III + TX1; Thiamethoxam + TX1; Kanamycin + TX1; Kasugamycin + TX1; Kasugamycin hydrochloride hydrate + TX1; Kinetin + TX1; Acetylpyridinium + TX1; Azoxystrobin + TX1; Bacillus thuringiensis subsp. Kustag + TX1;λ-Cypermethrin + TX1; Citrus scale insect parasitic wasp + TX1; Parafenoxam + TX1; Levamisole + TX1; Trimethyldioxane + TX1; Acetaminophen + TX1; Pesticide for the white armyworm + TX1; Clofenuron + TX1; Chlorfenapyr + TX1; Phosphate + TX1; m-isopropylphenyl methyl carbamate + TX1; Mirid bug + TX1; Magnesium phosphide + TX1; Malathion + TX1; Maleic hydrazine + TX1; Profenofibrate + TX1; Cabbage looper NPV + TX1; Mancozeb + TX1; Mancozeb + TX1; Tobramycin + TX1; Dimethomorph + TX1; Mancozeb + TX1; Azoxystrobin + TX1; Mebendazole + TX1; Phoxim + TX1; Tetramethrin + TX1; Acetylpyridinium + TX1; Chlorfluazuron + TX1; Megacodone + TX1; Meloxiconazole + TX1; Aphid-S-methyl + TX1; Cyfluthrin + TX1; Dithiamethoxam + TX1; Mepiquat chloride + TX1; Mepiquat chloride + TX1; Acaricide + TX1; Fenmethoxam + TX1; Mefenoxam + TX1; Metalaxyl + TX1; Metalaxyl-M + TX1; Metformin + TX1; Metformin-potassium + TX1; Metformin-sodium + TX1; Yellow-stalked flea + TX1; Metarhizium anisopliae (grasshopper variant) + TX1; Metarhizium anisopliae (beetle variant) + TX1; Methamidophos + TX1; Ethiophanate-methyl + TX1; Acaricide + TX1; Methamidophos + TX1; Sulfocarb + TX1; Phoxim + TX1; Mefenoxam + TX1; Thiophanate + TX1; Ethylphosphide + TX1; Dimethoate + TX1; Tebufenozide + TX1; Quinaldo + TX1; Cypermethrin + TX1; Methoxyfenozide + TX1; Sterilicide + TX1; Methyleugenol + TX1; Iodophos + TX1; Methylneodecanamide + TX1; Mancozeb + TX1; Methoxyfenozide + TX1; Dimethoate + TX1; Phenoxybenzone + TX1; Imidacloprid + TX1; Benomyl + TX1; Tetracycline + TX1; Dimethoate + TX1; Carbendazim + TX1; MGK 264 + TX1; Milbemycin + TX1; Milbemex + TX1; Phoxim + TX1; Morantyl Tartrate + TX1; Sterilidine + TX1; Moxifloxacin + TX1; Insecticidal + TX1; Acetazol + TX1; Mefenoxam + TX1; Varicella vesicanthoides composition + TX1;N-[2-[2,4-dichlorophenoxy]phenyl]-3-(difluoromethyl)-1-methyl-pyrazole-4-carboxamide + TX1; N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-[(2-isopropylphenyl)methyl]-1-methyl-pyrazole-4-carboxamide + TX1; Sodium mancozeb + TX1; Dibromophos + TX1; NC-170 + TX1; Namastem + TX1; European New Pine Sawfly NPV and Red-headed New Pine Sawfly NPV + TX1; Niclosamide-ethanolamine + TX1; Nicotine + TX1; Nicotine sulfate + TX1; Nicotinamide + TX1; Nitrazolium + TX1; Niethoxythiazole + TX1; Chloridine + TX1; Cypermethrin + TX1; Phthalosporin + TX1; Sodium thiamethoxam + TX1; Nornicotinamide + TX1; Fluorouracil + TX1; Polyfluorourea + TX1; Fluoropyrimidine + TX1; O,O,O',O'-Tetrapropyl dithiopyrophosphate + TX1; Octadecto-2,13-dien-1-yl acetate + TX1; Octadecto-2,13-dien-1-yl acetate + TX1; Octathiazoline + TX1; Furazolidone + TX1; Oleic acid + TX1; Omethoate + TX1; Heconazole + TX1; Small-flowered bug species + TX1; Oximethiophene + TX1; Osthol + TX1; Filacon + TX1; Oxysulfuron + TX1; Oxysulfuron + TX1; Oxysulfuron + TX1; Oxysulfuron + TX1; Oxysulfuron + TX1; Oxysulfuron + TX1; Oxysulfuron + TX1; Oxysulfuron + TX1; Quinoline copper + TX1; Oxadiazon + TX1; Oxazol + TX1; Oxytetracycline + TX1; Phosphate sulfoxide + TX1; Isofenphos + TX1; Phosphate sulfone + TX1; Oxytetracycline + TX1; Oxytetracycline dihydrate + TX1; Paclobutrazol + TX1; Paecilomyces roximate + TX1; Paraoxon + TX1; Parathion + TX1; Methyl parathion + TX1; Pabendazole + TX1; Isoprothiolane + TX1; Tebuconazole + TX1; Tebuconazole + TX1; Pendimethalin + TX1; Fluopyram + TX1; Pyraclostrobin + TX1; Permethrin + TX1; Petroleum + TX1; pH 60-38 + TX1; Cyazofamid + TX1; Indomethacin + TX1; Phosphate + TX1; Rat parathion + TX1; Phosphate + TX1; Thiophanate + TX1; Glyphosate + TX1; Imidacloprid + TX1; Chlorpyrifos + TX1; Phosphamidon + TX1; Fipronil + TX1; Phosphonic acid + TX1; Phosphorus + TX1; Phosphate + TX1; Methyl phoxim + TX1;Benzyl + TX1; Phytoseione gardica cochinchinensis + TX1; Tetraazolidinium + TX1; Azoxystrobin + TX1; Pimobendan + TX1; Warfarin + TX1; Piperaldehyde + TX1; Piperyl Butyl Ether + TX1; Synergistic Aldehyde + TX1; Methamidophos + TX1; Piperazine + TX1; Methylpyrimidin + TX1; Polycarbamate + TX1; Naphthylmethrin + TX1; Polyoxin B + TX1; Polyoxin D + TX1; Potassium Ethyl Xanthate + TX1; Potassium Hydroxyquinoline Sulfate + TX1; Praziquantel + TX1; Precipitin I + TX1; Precipitin II + TX1; Precipitin III + TX1; Aminopyrimidin + TX1; Thiamethoxam + TX1; Prochloraz + TX1; Iprodione + TX1; Profenofos + TX1; Procymidone + TX1 TX1; Cyclocarboxylic acid + TX1; Calcium cyclocarboxylic acid + TX1; Iprodione + TX1; Mancozeb + TX1; Propamid + TX1; Cymoxanil + TX1; Propanil + TX1; Acaricide + TX1; Phoxim + TX1; Propiconazole + TX1; Propyrazosulfuron + TX1; Propine + TX1; Propyrazosulfuron + TX1; Propyrazosulfuron + TX1; Propyrazosulfuron + TX1; Pymetrozine + TX1; Fluopyram + TX1; Pymetrozine + TX1; Pyrazosulfuron + TX1; Azoxystrobin + TX1; Pyrazosulfuron + TX1; Azoxystrobin + TX1; Diazoxystrobin + TX1; Azoxystrobin + TX1; Pyridabenamide + TX1; Bifenazate + TX1; Phoxim + TX1; Pyrazinone + TX1; Pyrethroids + TX1; Pyrethroid I + TX1; Pyrethroid II + TX1; Pyrethroid (natural product) + TX1; Pyrethroids (natural product) + TX1; Pyraclostrobin + TX1; Pyridaben + TX1; Flufenoxuron + TX1; Acetaminophen + TX1; Pyridaben ... TX1; Quinoline + TX1; Quinoline-methyl + TX1; Alginate + TX1; Quinofram + TX1; Quinopamine + TX1; Quinoline + TX1; Quinoline + TX1; Pentachloronitrobenzene + TX1;R-1492 +TX1; R-Methoxyfen + TX1; Polygonum cuspidatum extract + TX1; Ribavirin + TX1; Rotenone + TX1; Ranidin (Ranidin) + TX1; Veratrum saba + TX1; Octapoxetine + TX1; Onychoside + TX1; Cymoxanil + TX1; Fluoxetine + TX1; Silaclofen + TX1; Synergistic powder + TX1; Sesamol + TX1; Phenytoin + TX1; Phenytoin + TX1; Flusilazole + TX1; Silthiamethoxam + TX1; Silomethasone + TX1; Sodium Tetrathionate + TX1; Threphalosporin + TX1; Sodium Sulfide + TX1; Spinosad + TX1; Spirodiclofen + TX1; Spirodiclofen + TX1; Spirotetramethrin + TX1; Spirocyclohexane + TX1; *Nematodeus fasciatus* + TX1; *Nematodeus stearothermium* + TX1; *Nematodeus stearothermium* + TX1; *Nematodeus griseus* + TX1; *Nematodeus rippi* + TX1; *Nematodeus reesei* + TX1; *Nematodeus stearothermium* + TX1; *Nematodeus stearothermium* species + TX1; Streptomycin + TX1; Streptomycin sesquisulfate + TX1; Bacterial methyl ether + TX1; Sulfodioxanone + TX1; Sulfate + TX1; Sulfate + TX1; Thiophanate + TX1; Tar + TX1; T-flumethomorph + TX1; TCMTB + TX1; TDE + TX1; Tebuconazole + TX1; Tebufenozide + TX1; Pyridaben + TX1; Isobutylethoxyquinoline + TX1; Butylpyrimidine + TX1; Tetrachloronitrobenzene + TX1; Fluorouracil + TX1; Heptamethrin + TX1; Dithion + TX1; Cypermethrin + TX1; Terbufos + TX1; Terbufos + TX1; Insecticidal + TX1; Flufenoxuron + TX1; Tetradec-11-en-1-ylacetate + TX1; Tetrachlorfon + TX1; Acephate + TX1; Tetrafluthrin + TX1; Acaricide + TX1; Thiamethoxam + TX1; Thiamethoxam + TX1; Thiamethoxam + TX1; Thiamethoxam + TX1; Thiazidophos + TX1; Thiamethoxam + TX1; Thifluzamide + TX1; Insecticidal + TX1; Insecticidal Cyclochlor + TX1; Insecticidal Cyclochlor Oxalate + TX1; Thiamethoxam + TX1; Dimethoate + TX1; Methyl phorate + TX1; Thiophanate-methyl + TX1; Methyl thiophanate + TX1; Acaricide + TX1; Carbohydrate + TX1; Carbohydrate-disodium + TX1; Thiamethoxam + TX1; Thiamethoxam + TX1; Tiamulin + TX1; Tiomede + TX1;Methyl thiophanate + TX1; azoxystrobin + TX1; trifluoperoxynil + TX1; parathion + TX1; tetrabromopyr + TX1; transchlorpyrifos + TX1; tratamidophos + TX1; triadimefon + TX1; triadimefon + TX1; triazophos + TX1; pymetrozine + TX1; triazophos + TX1; imidacloprid + TX1; defoliant + TX1; trichlorfon + TX1; isofenphos-3 + TX1; phosphamidon + TX1; Trichogramma spp. + TX1; trichlorobenzazole + TX1; chlorpyrifos + TX1; tricyclazole + TX1; tridemorph + TX1; serotributamol + TX1; azoxystrobin + TX1; fluopyram + TX1; chlorfenapyr + TX1; azoxystrobin + TX1; Mediterranean fruit fly attractant + TX1; Mediterranean fruit fly attractant A + TX1; Mediterranean fruit fly attractant B1 + TX1; Mediterranean fruit fly attractant B2 + TX1; Mediterranean fruit fly attractant C + TX1; Mixed carbendazim + TX1; Trichloroisocyanuric acid + TX1; Anti-rot ester + TX1; Anti-rot ester-ethyl + TX1; Imidacloprid + TX1; Mefenoxam + TX1; Chuangke + TX1; Tobramycin + TX1; Western blind mite + TX1; Uniconazole + TX1; Urethroid + TX1; Effectivemycin + TX1; Valamidine + TX1; Aphidicide + TX1; Mefenoxam + TX1; Veratrine + TX1; Veratrine + TX1; Synergistic alkyne + TX1; Verticillium clavatum + TX1; Ethylsuccinate + TX1; XMC + TX1; Xylenol + TX1; Zeatin + TX1; ζ-Cypermethrin + TX1; Kasugamycin + TX1; Zinc naphthenate + TX1; Thiazole zinc + TX1; Zineb + ​​TX1; Zinc thiophanate + TX1; Azoxystrobin + TX1; Benzoylamidol + TX1; 2-(Difluoromethyl)-N-[(3S)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (this compound can be prepared by the method described in WO 2014 / 095675) + TX1; 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1,2,4-triazol-1-ylmethyl)cyclopentanecarboxylate (this compound can be prepared by the method described in WO 2019 / 093522) + TX1; (2R)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propionate methyl ester (this compound can be prepared by the method described in WO 2019 / 093522) + TX1;5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)cyclopropyl]pyrimidin-2-amine (this compound can be prepared by the method described in WO 2021 / 255093) + TX1; aminolpyridine (this compound can be prepared by the method described in WO 2014 / 006945) + TX1; thiamethoxam (this compound can be prepared by the method described in WO 2011 / 138281) + TX1; 1-[6-(difluoromethyl)-5-methyl-3-pyridyl]-4,4-difluoro-3,3-dimethyl-isoquinoline (this compound can be prepared by the method described in WO 2017 / 016915) + TX1; 1-[4-(difluoromethoxy)-2-methyl-phenyl]-2-(1,2,4-triazol-1-yl)-1-[1-(trifluoromethyl)cyclopropyl]ethanol (this compound can be prepared by the method described in WO 2021 / 249800) + TX1; 1-[2-chloro-4-(difluoromethoxy)phenyl]-2-(1,2,4-triazol-1-yl)-1-[1-(trifluoromethyl)cyclopropyl]ethanol (this compound can be prepared by the method described in WO 2021 / 249800) + TX1; 1-(5,6-dimethyl-3-pyridyl)-4,4-difluoro-3,3-dimethyl-isoquinoline (this compound can be prepared by the method described in WO 2017 / 016915) + TX1; N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzylthiocarboxamide (this compound can be prepared by the method described in WO 2015 / 185485) + TX1; 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide (this compound can be prepared by the method described in WO 2017 / 178245) + TX1; fluopyram + TX1; N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzylcarboxamide (this compound can be prepared by the method described in WO 2015 / 185485) + TX1; (Z,2E)-5-[1-(2,4-dichlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide (this compound can be prepared by the method described in WO 2018 / 153707) + TX1; (Z,2E)-5-[1-(4-chlorophenyl)pyrazol-3-yl]oxy-2-methoxyimino-N,3-dimethyl-pent-3-enamide (this compound can be prepared by the method described in WO 2013 / 092224) + TX1;(2E)-2-methoxyimino-2-[3-methyl-2-[[(E)-1-[4-(trifluoromethyl)-2-pyridyl]ethyleneamino]oxymethyl]phenyl]methyl acetate (this compound can be prepared by the method described in WO 2022 / 033906) + TX1; (2E)-2-methoxyimino-N-methyl-2-[3-methyl-2-[[(E)-1-[4-(trifluoromethyl)-2-pyridyl]ethyleneamino]oxymethyl]phenyl]acetamide (this compound can be prepared by the method described in WO 2022 / 033906) + TX1; (2E)-2-[2-[[(E)-[3-(4-fluorophenyl)-1-methyl-prop-2-ynylene]amino]oxymethyl]-3-methyl-phenyl]-2-methoxyimino-N-methyl-acetamide (this compound can be prepared by WO 2022 / 033906) + TX1; (2E)-2-[2-[[(E)-[3-(4-fluorophenyl)-1-methyl-prop-2-ynylene]amino]oxymethyl]-3-methyl-phenyl]-2-methoxyimino-N-methyl-acetamide (this compound can be prepared by WO 2022 / 033906) + TX1; (Prepared by the method described in WO 2021 / 249928) + TX1; (2E)-2-[2-[[(E)-[3-(4-fluorophenyl)-1-methyl-prop-2-ynyne]amino]oxymethyl]-3-methyl-phenyl]-2-methoxyimino-acetic acid methyl ester (This compound can be prepared by the method described in WO 2021 / 249928) + TX1; 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-propyl]imidazolium-4-carboxylonitrile (This compound can be prepared by the method described in WO 2016 / 156290) + TX1; 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxy-propyl]imidazolium-4-carboxylonitrile (This compound can be prepared by the method described in WO 2016 / 156290) + TX1; 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)prop-2-ol (This compound can be prepared by the method described in WO 2017 / 029179) + TX1; 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)prop-2-ol (This compound can be prepared by the method described in WO 2017 / 029179) + TX1; 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)ethyl]pyrimidin-2-amine (This compound can be prepared by the method described in WO 2021 / 255093) + TX1; 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(3,5-difluorophenyl)ethyl]pyrimidin-2-amine (this compound can be prepared by the method described in WO 2021 / 255093) + TX1;N-[1-(2-fluorophenyl)cyclopropyl]-5-[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]pyrimidin-2-amine (this compound can be prepared by the method described in WO 2021 / 255093) + TX1; 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)ethyl]pyrimidin-2-amine (this compound can be prepared by the method described in WO 2021 / 255093) + TX1; 2-(difluoromethyl)-5-[2-[1-(2,6-difluorophenyl)cyclopropoxy]pyrimidin-5-yl]-1,3,4-oxadiazole (this compound can be prepared by the method described in WO 2021 / 255093) + TX1; 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)cyclopropyl]pyrimidin-2-amine (This compound can be prepared by the method described in WO 2021 / 255093) + TX1; 5-[(4-bromo-2-methyl-phenyl)methyl]-3-[3-(3-chloro-2-fluoro-phenoxy)-6-methyl-pyridazin-4-yl]-5,6-dihydro-4H-1,2,4-oxadiazine (This compound can be prepared by the method described in WO 2021 / 255070) + TX1; 3-[3-(3-cyclopropyl-2-fluoro-phenoxy)-6-methyl-pyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine (This compound can be prepared by the method described in WO 2021 / 255093) + TX1; 3-[3-(3-cyclopropyl-2-fluoro-phenoxy)-6-methyl-pyridazin-4-yl]-5-[(2,4-dimethylphenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine (This compound can be prepared by the method described in WO 2021 / 255093) (Prepared by the method described in WO 2021 / 255070) + TX1; N-(2,2,2-trifluoroethyl)-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]oxazol-4-carboxamide (This compound can be prepared by the method described in WO 2022 / 133114) + TX1; 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenoxy]methyl]pyrazole-4-carboxylic acid ethyl ester (This compound can be prepared by the method described in WO 2022 / 133114) + TX1; 1-[[4-[(Z)-2-ethoxy-3,3,3-trifluoro-prop-1-enoxy]phenyl]methyl]pyrazole-4-carboxylic acid ethyl ester (This compound can be prepared by WO 2022 / 133114) Prepared by the methods described in WO 2020 / 056090 and WO 2021 / 183707) + TX1; 1-[[4-[[2-(trifluoromethyl)-1,3-dioxolane-2-yl]methoxy]phenyl]methyl]pyrazole-4-carboxylic acid ethyl ester (this compound can be prepared by the methods described in WO 2020 / 056090 and WO 2021 / 183707) + TX1;Methyl N-[[5-[4-(2,4-dimethylphenyl)triazol-2-yl]-2-methyl-phenyl]methyl]carbamate (this compound can be prepared by the method described in WO 2020 / 097012) + TX1; 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 WO 2020 / 097012) + TX1; Methyl N-[[5-[1-(4-cyclopropyl-2,6-difluoro-phenyl)pyrazol-3-yl]-2-methyl-phenyl]methyl]carbamate (this compound can be prepared by the method described in WO 2020 / 097012) + TX1; Methyl N-[[5-[1-(4-cyclopropyl-2,6-difluoro-phenyl)pyrazol-3-yl]-2-methyl-phenyl]methyl]carbamate (this compound can be prepared by the method described in WO 2020 / 097012) + TX1; methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propionate (this compound can be prepared by the method described in WO 2019 / 093522) + TX1; 4,4,5-trifluoro-3,3-dimethyl-1-(3-quinolinyl)isoquinoline + TX1; 5-fluoro-3,3,4,4-tetramethyl-1-(3-quinolinyl)isoquinoline + TX1; 2-methoxy-N-[methoxy-[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]acetamide (this compound can be prepared by the method described in WO 2020 / 256113) + TX1; N-[methoxy-[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]-2-methyl-propionamide (this compound can be prepared by the method described in WO 2020 / 256113) + TX1; N-[methoxy-[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]butyramide (this compound can be prepared by the method described in WO 2020 / 256113) + TX1; 2-(difluoromethyl)-N-[(3R)-3-ethyl-1,1-dimethyl-indan-4-yl]pyridine-3-carboxamide (this compound can be prepared by the method described in WO 2014 / 095675) + TX1; 2-(difluoromethyl)-N-(3-ethyl-1,1-dimethyl-indan-4-yl)pyridine-3-carboxamide (this compound can be prepared by the method described in WO 2014 / 095675) + TX1; 2-(difluoromethyl)-N-(1,1,3-trimethylindan-4-yl)pyridine-3-carboxamide + TX1;(5R)-3-[3-(3-chloro-2-fluoro-phenoxy)-6-methyl-pyridazin-4-yl]-5-[(2-chloro-4-methyl-phenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine (this compound can be prepared by the methods described in WO 2020 / 127780 and WO 2021 / 255070) + TX1; (5S)-3-[3-(3-chloro-2-fluoro-phenoxy)-6-methyl-pyridazin-4-yl]-5-[(2-chloro-4-methyl-phenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine (this compound can be prepared by the methods described in WO 2020 / 127780 and WO 2021 / 255070) + TX1; 3-[3-(3-chloro-2-fluoro-phenoxy)-6-methyl-pyridazin-4-yl]-5-[(2-chloro-4-methyl-phenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine (this compound can be prepared by the methods described in WO 2020 / 127780, WO 2021 / 255070) + TX1; (Z)-3-methoxy-2-(2-methyl-5-phenyl-phenoxy)prop-2-enoic acid methyl ester (this compound can be prepared by the methods described in JP2023078251) + TX1; 2-[(2,6-difluoro-4-pyridinyl)-(2-methylpropionyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazol-4-carboxamide + TX1; or its (R) or (S) enantiomers or mixtures + TX1 (this compound can be prepared by the methods described in WO 2017207362 A1, WO 2019105933 A1, WO 2020109511 A1, WO2021244952 A1); 2-[(2,6-difluoro-4-pyridinyl)-(tetrahydropyran-4-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazolyl-4-carboxamide + TX1; or its (R) or (S) enantiomers or mixtures thereof + TX1 (this compound can be prepared by the methods described in WO 2017207362 A1, WO 2019105933 A1, WO 2020109511 A1, WO2021244952 A1). Prepared by the method described in A1); 2-[cyano-(2,6-difluoro-4-pyridinyl)amino]-5-methyl-N-spiro[3,4]octane-3-yl-thiazolyl-4-carboxamide + TX1; or its (R) or (S) enantiomers or mixtures + TX1 (this compound can be prepared by the method described in WO 2017207362 A1, WO 2019105933 A1, WO 2020109509 A1);2-[cyano-(2,6-difluoro-4-pyridinyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazol-4-carboxamide + TX1; or its (R) or (S) enantiomers or mixtures + TX1 (this compound can be prepared by the methods described in WO 2017207362 A1, WO 2019105933 A1, WO 2020109509 A1); 2-[(2,6-difluoro-4-pyridinyl)-(2-methoxyacet ...WO 2-[(2,6-difluoro-4-pyridinyl)-(2-methoxyacetyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazol-4-carboxamide + TX1; or its (R) or (S) enantiomers or mixtures + TX1 (this compound Prepared by the methods described in WO 2020109511 A1, WO 2021244952 A1); 2-[acetyl-(2,6-difluoro-4-pyridyl)amino]-5-methyl-N-spiro[3,4]octane-3-yl-thiazolyl-4-carboxamide + TX1; or its (R) or (S) enantiomers or mixtures + TX1 (this compound can be prepared by the methods described in WO 2017207362 A1, WO 2019105933 A1, WO 2020109511A1, WO 2021244952 A1); N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide (this compound can be prepared by the methods described in WO 2017 / 055473) + TX1; (Z)-2-(5-cyclopentyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester (this compound can be prepared by the method described in WO 2020 / 193387) + TX1; (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester (this compound can be prepared by the method described in WO 2020 / 193387) + TX1; N-[(1R)-1-benzyl-1,3-dimethylbutyl]-8-fluoroquinoline-3-carboxamide (this compound can be prepared by the method described in WO 2017 / 153380) + TX1; N-[(1S)-1-benzyl-1,3-dimethylbutyl]-8-fluoroquinoline-3-carboxamide (this compound can be prepared by the method described in WO 2017 / 153380) + TX1; 2-[(2,6-difluoro-4-pyridinyl)-(oxetane-3-carbonyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazol-4-carboxamide + TX1;Or its (R) or (S) enantiomers or mixtures + TX1 (this compound can be prepared by the methods described in WO 2017207362 A1, WO 2019105933 A1, WO2020109511 A1, WO 2021244952 A1); 2-[acetyl-(2,6-difluoro-4-pyridinyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazolyl-4-carboxamide + TX1; or its (R) or (S) enantiomers or mixtures + TX1 (this compound can be prepared by the methods described in WO 2017207362 A1, WO 2019105933 A1, WO 2020109511 A1, WO 2021244952 A1); 2-[acetyl-(2,6-difluoro-4-pyridinyl)amino]-N-(2,2-dimethylcyclobutyl)-5-methyl-thiazolyl-4-carboxamide + TX1; or its (R) or (S) enantiomers or mixtures + TX1 (this compound can be prepared by the methods described in WO 2017207362 A1, WO 2019105933 A1, WO 2020109511 A1, WO 2021244952 A1); Prepared by the method described in A1); N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide + TX1; or its (R) or (S) enantiomers or mixtures + TX1 (this compound can be prepared by the method described in WO 2017 / 055473).

[0184] In another aspect of the invention, an antifungal composition is provided comprising a mixture of a crystalline polymorph (form A) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein, and component (B) as an active ingredient, wherein component (B) It is a compound selected from the group consisting of the following, or its salts, enantiomers, tautomers, or N-oxides: bifenthiopyrrolidone, aramidobenzene, aramidobenzene-S-methyl, copper sulfate, copper hydroxide, copper oxychloride, copper oxide, cyproconazole, difenoconazole, hexaconazole, prothioconazole, propiconazole, tebuconazole, flutriafol, benzyl benzoate, pyraclostrobin, azoxystrobin, oxadiazon, pyraclostrobin, pyraclostrobin, mancozeb, chlorothalonil, fluazinam, fluazinam, pyraclostrobin, fluazinam, fluazinam, fluazinam, benzoxazole, benzo[a]fluoroquinolones, fluazinam hydroxylamine, isopropoxyfenozide, fluindazole, indomethacin, chlorfluazon, pyridabenamide, methylarylpyridinamide, and tetrazolium.

[0185] Preferably, a fungicidal composition is provided comprising a mixture of a crystalline polymorph (form A) of methyl 2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein, and a component (B) as an active ingredient, wherein component (B) is a compound selected from the group consisting of: aramalic acid-benzene-S-methyl, cyproconazole, difenoconazole, hexaconazole, prothioconazole, tebuconazole, benzyloxydine, azoxystrobin, oxadiazon, mancozeb, chlorothalonil, fluazinam, fluoxazin, benzoylfluopyram, fluopyram, benzoylfluopyram, fluopyram, methyl arylpyridinamide, and tetrazolium.

[0186] More preferably, a fungicidal composition is provided comprising a mixture of a crystalline polymorph (form A) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein, and a component (B) as an active ingredient, wherein component (B) is a compound selected from the group consisting of, or a salt, enantiomer, tautomer, or N-oxide thereof: cycloproconazole, difenoconazole, prothioconazole, tebuconazole, benzyl benzoate, mancozeb, chlorothalonil, and fluopyram.

[0187] Even more preferably, a fungicidal composition is provided comprising a mixture of a crystalline polymorph (form A) of methyl 2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein, and a component (B) as an active ingredient, wherein component (B) is a compound selected from the group consisting of a salt, enantiomer, tautomer, or N-oxide thereof: difenoconazole, prothioconazole, tebuconazole, benzyl benzoate, and chlorothalonil.

[0188] In another aspect of the invention, a fungicidal composition is provided comprising a mixture of a crystalline polymorph (form A) of methyl 2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein, and a component (B) as an active ingredient, wherein component (B) is a compound selected from the group consisting of: bifenthionil, aramidobenzene, aramidobenzene-S-methyl, copper sulfate, copper hydroxide, copper oxychloride, copper oxide, cyproconazole, difenoconazole, hexaconazole, prothioconazole, propiconazole, tebuconazole, flutriafol, benzyl benzoate, butyl morpholine, azoxystrobin, fenpropathrin, oxadiazon, azoxystrobin, pyraclostrobin, mancozeb, chlorothalonil, fluazinam, fluazinam, fluazinam, pyraclostrobin, pyraclostrobin Amines, fluoxetine, boscalid, fluoxazine, benzovindiflupyr, fluoxetine hydroxylamine, isopropoxypyridine, fluinbazin, indoxacarb, chlorfluazin, pyridazinamide, methyl arylpyridazinamide, tetrazolium, (5R)-3-[3-(3-chloro-2-fluoro-phenoxy)-6-methyl-pyridazin-4-yl]-5-[(2-chloro-4-methyl-phenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine (this compound can be derived from WO4) (This compound can be prepared by the methods described in WO 2020 / 127780 and WO 2021 / 255070), (5S)-3-[3-(3-chloro-2-fluoro-phenoxy)-6-methyl-pyridazin-4-yl]-5-[(2-chloro-4-methyl-phenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine (this compound can be prepared by the methods described in WO 2020 / 127780 and WO 2021 / 255070), ... The following compounds can be prepared by the method described in 2021 / 255070: methyl (Z)-3-methoxy-2-(2-methyl-5-phenyl-phenoxy)prop-2-enoate (this compound can be prepared by the method described in JP 2023078251), ethyl 1-[[4-[[2-(trifluoromethyl)-1,3-dioxolane-2-yl]methoxy]phenyl]methyl]-1H-pyrazole-4-carboxylate (this compound can be prepared by the method described in WO 2021 / 183707), ethyl 1-[[4-[[(1Z)-2-ethoxy-3,3,3-trifluoro-1-propen-1-yl]oxy]phenyl]methyl]-1H-pyrazole-4-carboxylate (this compound can be prepared by the method described in WO 2021 / 183707), 5-[5-(difluoromethyl)-1,3,4-Oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)ethyl]pyrimidin-2-amine (this compound can be prepared by the method described in WO 2021 / 255093), 2-(difluoromethyl)-5-[2-[1-(2,6-difluorophenyl)cyclopropoxy]pyrimidin-5-yl]-1,3,4-oxadiazole (this compound can be prepared by the method described in WO 2021 / 255093), 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)cyclopropyl]pyrimidin-2-amine (this compound can be prepared by the method described in WO 2021 / 255093), 2-(difluoromethyl)-5-[2-[1-(2,6-difluorophenyl)cyclopropyl]pyrimidin-2-amine (this compound can be prepared by the method described in WO 2021 / 255093), 2-(difluoromethyl)-5-[2-[1-(2,6-difluorophenyl)cyclopropyl]pyrimidin-2-amine (this compound can be prepared by the method described in WO 2021 / 255093), 2-(difluoromethyl)-5-[2-[1-(2,6-difluorophenyl)cyclopropyl]pyrimidin-2-amine), 2-(difluoromethyl)-5 ... The compounds can be prepared by the methods described in WO 2021 / 255093, such as 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)cyclopropyl]pyrimidin-2-amine (this compound can be prepared by the methods described in WO 2021 / 255093), N-[1-(2-fluorophenyl)cyclopropyl]-5-[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]pyrimidin-2-amine (this compound can be prepared by the methods described in WO 2021 / 255093), and 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)ethyl]pyrimidin-2-amine (this compound can be prepared by the methods described in WO 2021 / 255093). The following compounds can be prepared by the method described in WO 2021 / 255093: 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(3,5-difluorophenyl)ethyl]pyrimidin-2-amine (this compound can be prepared by the method described in WO 2021 / 255093), and N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropaneformamide (this compound can be prepared by WO 2021 / 255093). The following compounds can be prepared by the method described in WO 2017 / 055473: N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide, or their (R) or (S) enantiomers or mixtures thereof (this compound can be prepared by the method described in WO 2017 / 055473), methyl 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1,2,4-triazol-1-ylmethyl)cyclopentanecarboxylate (this compound can be prepared by WO 2017 / 055473). Methyl (2R)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propionate (this compound can be prepared by the method described in WO2019 / 093522); 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-Triazol-1-yl)methyl propionate (this compound can be prepared by the method described in WO 2019 / 093522), 1-[4-(difluoromethoxy)-2-methyl-phenyl]-2-(1,2,4-triazol-1-yl)-1-[1-(trifluoromethyl)cyclopropyl]ethanol (this compound can be prepared by the method described in WO 2019 / 093522), Methyl acetate (prepared by the method described in WO2021 / 249800), (2E)-2-methoxyimino-2-[3-methyl-2-[[(E)-1-[4-(trifluoromethyl)-2-pyridyl]ethyleneamino]oxymethyl]phenyl]acetamide (this compound can be prepared by the method described in WO2022 / 033906), (2E)-2-methoxyimino-N-methyl-2-[3-methyl-2-[[(E)-1-[4-(trifluoromethyl)-2-pyridyl]ethyleneamino]oxymethyl]phenyl]acetamide (this compound can be prepared by the method described in WO2022 / 249800). Methyl acetate (2E)-2-[2-[[(E)-[3-(4-fluorophenyl)-1-methyl-prop-2-ynyne]amino]oxymethyl]-3-methyl-phenyl]-2-methoxyimino-acetate (this compound can be prepared by methods such as those described in WO2021 / 249928), and N-methylacetamide (2E)-2-[2-[[(E)-[3-(4-fluorophenyl)-1-methyl-prop-2-ynyne]amino]oxymethyl]-3-methyl-phenyl]-2-methoxyimino-N-methylacetamide (this compound can be prepared by methods such as those described in WO2021 / 249928). Methyl carbamate (prepared by the method described in WO 2021 / 249928), 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 WO 2020 / 097012), N-[[5-[1-(4-cyclopropyl-2,6-difluoro-phenyl)pyrazol-3-yl]-2-methyl-phenyl]methyl]carbamate (this compound can be prepared by the method described in WO 2020 / 097012), N-[methoxy-[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]butyramide (this compound can be prepared by the method described in WO 2020 / 097012), N-[methoxy-[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]butyramide (this compound can be prepared by the method described in WO 2021 / 249928), N-[methoxy-[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]butyramide (this compound can be prepared by the method described in WO 2020 / 097012 ... The following compounds can be prepared using the methods described in WO 2020 / 256113: 2-methoxy-N-[methoxy-[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]acetamide (this compound can be prepared using the methods described in WO 2020 / 256113) and N-[methoxy-[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]-2-methylpropionamide (this compound can be prepared using the methods described in WO 2020 / 256113).

[0189] In another aspect of the invention, an antifungal composition is provided comprising a mixture of a crystalline polymorph (form B) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein, and component (B) as an active ingredient, wherein component (B) It is a compound selected from the group consisting of the following, or its salts, enantiomers, tautomers, or N-oxides: bifenthiopyrrolidone, aramidobenzene, aramidobenzene-S-methyl, copper sulfate, copper hydroxide, copper oxychloride, copper oxide, cyproconazole, difenoconazole, hexaconazole, prothioconazole, propiconazole, tebuconazole, flutriafol, benzyl benzoate, pyraclostrobin, azoxystrobin, oxadiazon, pyraclostrobin, pyraclostrobin, mancozeb, chlorothalonil, fluazinam, fluazinam, pyraclostrobin, fluazinam, fluazinam, fluazinam, benzoxazole, benzo[a]fluoroquinolones, fluazinam hydroxylamine, isopropoxyfenozide, fluindazole, indomethacin, chlorfluazon, pyridabenamide, methylarylpyridinamide, and tetrazolium.

[0190] Preferably, a fungicidal composition is provided comprising a mixture of a crystalline polymorph (form B) of methyl 2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein, and component (B) as an active ingredient, wherein component (B) is a compound selected from the group consisting of: aramalic acid-benzene-S-methyl, cyproconazole, difenoconazole, hexaconazole, prothioconazole, tebuconazole, benzyloxydine, azoxystrobin, oxadiazon, mancozeb, chlorothalonil, fluazinam, fluoxazin, benzoylfluopyram, fluopyram, benzoylfluopyram, fluopyram, methyl arylpyridinamide, and tetrazolium.

[0191] More preferably, a fungicidal composition is provided comprising a mixture of a crystalline polymorph (form B) of methyl 2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein, and component (B) as an active ingredient, wherein component (B) is a compound selected from the group consisting of, or a salt, enantiomer, tautomer, or N-oxide thereof: cycloproconazole, difenoconazole, prothioconazole, tebuconazole, benzyl benzoate, mancozeb, chlorothalonil, and fluopyram.

[0192] Even more preferably, a fungicidal composition is provided comprising a mixture of a crystalline polymorph (form B) of methyl 2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein, and component (B) as an active ingredient, wherein component (B) is a compound selected from the group consisting of, or a salt thereof, enantiomer, tautomer, or N-oxide thereof: difenoconazole, prothioconazole, tebuconazole, benzyl benzoate, and chlorothalonil.

[0193] In another aspect of the invention, a fungicidal composition is provided comprising a mixture of a crystalline polymorph (form B) of methyl 2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein, and component (B) as an active ingredient, wherein component (B) is a compound selected from the group consisting of: bifenthionil, aramidobenzene, aramidobenzene-S-methyl, copper sulfate, copper hydroxide, copper oxychloride, copper oxide, cyproconazole, difenoconazole, hexaconazole, prothioconazole, propiconazole, tebuconazole, flutriafol, benzyl benzoate, butyl morpholine, azoxystrobin, fenpropathrin, oxadiazon, azoxystrobin, pyraclostrobin, mancozeb, chlorothalonil, fluazinam, fluazinam, fluazinam, pyraclostrobin, pyraclostrobin Amines, fluoxetine, boscalid, fluoxazine, benzovindiflupyr, fluoxetine hydroxylamine, isopropoxypyridine, fluinbazin, indoxacarb, chlorfluazin, pyridazinamide, methyl arylpyridazinamide, tetrazolium, (5R)-3-[3-(3-chloro-2-fluoro-phenoxy)-6-methyl-pyridazin-4-yl]-5-[(2-chloro-4-methyl-phenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine (this compound can be derived from WO4) (This compound can be prepared by the methods described in WO 2020 / 127780 and WO 2021 / 255070), (5S)-3-[3-(3-chloro-2-fluoro-phenoxy)-6-methyl-pyridazin-4-yl]-5-[(2-chloro-4-methyl-phenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine (this compound can be prepared by the methods described in WO 2020 / 127780 and WO 2021 / 255070), ... The following compounds can be prepared by the method described in 2021 / 255070: methyl (Z)-3-methoxy-2-(2-methyl-5-phenyl-phenoxy)prop-2-enoate (this compound can be prepared by the method described in JP 2023078251), ethyl 1-[[4-[[2-(trifluoromethyl)-1,3-dioxolane-2-yl]methoxy]phenyl]methyl]-1H-pyrazole-4-carboxylate (this compound can be prepared by the method described in WO 2021 / 183707), ethyl 1-[[4-[[(1Z)-2-ethoxy-3,3,3-trifluoro-1-propen-1-yl]oxy]phenyl]methyl]-1H-pyrazole-4-carboxylate (this compound can be prepared by the method described in WO 2021 / 183707), 5-[5-(difluoromethyl)-1,3,4-Oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)ethyl]pyrimidin-2-amine (this compound can be prepared by the method described in WO 2021 / 255093), 2-(difluoromethyl)-5-[2-[1-(2,6-difluorophenyl)cyclopropoxy]pyrimidin-5-yl]-1,3,4-oxadiazole (this compound can be prepared by the method described in WO 2021 / 255093), 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)cyclopropyl]pyrimidin-2-amine (this compound can be prepared by the method described in WO 2021 / 255093), 2-(difluoromethyl)-5-[2-[1-(2,6-difluorophenyl)cyclopropyl]pyrimidin-2-amine (this compound can be prepared by the method described in WO 2021 / 255093), 2-(difluoromethyl)-5-[2-[1-(2,6-difluorophenyl)cyclopropyl]pyrimidin-2-amine (this compound can be prepared by the method described in WO 2021 / 255093), 2-(difluoromethyl)-5-[2-[1-(2,6-difluorophenyl)cyclopropyl]pyrimidin-2-amine), 2-(difluoromethyl)-5 ... The compounds can be prepared by the methods described in WO 2021 / 255093, such as 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)cyclopropyl]pyrimidin-2-amine (this compound can be prepared by the methods described in WO 2021 / 255093), N-[1-(2-fluorophenyl)cyclopropyl]-5-[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]pyrimidin-2-amine (this compound can be prepared by the methods described in WO 2021 / 255093), and 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)ethyl]pyrimidin-2-amine (this compound can be prepared by the methods described in WO 2021 / 255093). The following compounds can be prepared by the method described in WO 2021 / 255093: 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(3,5-difluorophenyl)ethyl]pyrimidin-2-amine (this compound can be prepared by the method described in WO 2021 / 255093), and N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropaneformamide (this compound can be prepared by WO 2021 / 255093). The following compounds can be prepared by the method described in WO 2017 / 055473: N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide, or their (R) or (S) enantiomers or mixtures thereof (this compound can be prepared by the method described in WO 2017 / 055473), methyl 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1,2,4-triazol-1-ylmethyl)cyclopentanecarboxylate (this compound can be prepared by WO 2017 / 055473). Methyl (2R)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propionate (this compound can be prepared by the method described in WO2019 / 093522); 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-Triazol-1-yl)methyl propionate (this compound can be prepared by the method described in WO 2019 / 093522), 1-[4-(difluoromethoxy)-2-methyl-phenyl]-2-(1,2,4-triazol-1-yl)-1-[1-(trifluoromethyl)cyclopropyl]ethanol (this compound can be prepared by the method described in WO 2019 / 093522), Methyl acetate (prepared by the method described in WO2021 / 249800), (2E)-2-methoxyimino-2-[3-methyl-2-[[(E)-1-[4-(trifluoromethyl)-2-pyridyl]ethyleneamino]oxymethyl]phenyl]acetamide (this compound can be prepared by the method described in WO2022 / 033906), (2E)-2-methoxyimino-N-methyl-2-[3-methyl-2-[[(E)-1-[4-(trifluoromethyl)-2-pyridyl]ethyleneamino]oxymethyl]phenyl]acetamide (this compound can be prepared by the method described in WO2022 / 249800). Methyl acetate (2E)-2-[2-[[(E)-[3-(4-fluorophenyl)-1-methyl-prop-2-ynyne]amino]oxymethyl]-3-methyl-phenyl]-2-methoxyimino-acetate (this compound can be prepared by methods such as those described in WO2021 / 249928), and N-methylacetamide (2E)-2-[2-[[(E)-[3-(4-fluorophenyl)-1-methyl-prop-2-ynyne]amino]oxymethyl]-3-methyl-phenyl]-2-methoxyimino-N-methylacetamide (this compound can be prepared by methods such as those described in WO2021 / 249928). Methyl carbamate (prepared by the method described in WO 2021 / 249928), 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 WO 2020 / 097012), N-[[5-[1-(4-cyclopropyl-2,6-difluoro-phenyl)pyrazol-3-yl]-2-methyl-phenyl]methyl]carbamate (this compound can be prepared by the method described in WO 2020 / 097012), N-[methoxy-[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]butyramide (this compound can be prepared by the method described in WO 2020 / 097012), N-[methoxy-[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]butyramide (this compound can be prepared by the method described in WO 2021 / 249928), N-[methoxy-[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]butyramide (this compound can be prepared by the method described in WO 2020 / 097012 ... The following compounds can be prepared using the methods described in WO 2020 / 256113: 2-methoxy-N-[methoxy-[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]acetamide (this compound can be prepared using the methods described in WO 2020 / 256113) and N-[methoxy-[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]-2-methylpropionamide (this compound can be prepared using the methods described in WO 2020 / 256113).

[0194] In another aspect of the invention, an antifungal composition is provided comprising a mixture of a crystalline polymorph (form C) of methyl 2-(5-cyclohexyl-2-methylphenoxy)-3-methoxy-prop-2-enoate as defined herein, and component (B) as an active ingredient, wherein component (B) It is a compound selected from the group consisting of the following, or its salts, enantiomers, tautomers, or N-oxides: bifenthiopyrrolidone, aramidobenzene, aramidobenzene-S-methyl, copper sulfate, copper hydroxide, copper oxychloride, copper oxide, cyproconazole, difenoconazole, hexaconazole, prothioconazole, propiconazole, tebuconazole, flutriafol, benzyl benzoate, pyraclostrobin, azoxystrobin, oxadiazon, pyraclostrobin, pyraclostrobin, mancozeb, chlorothalonil, fluazinam, fluazinam, pyraclostrobin, fluazinam, fluazinam, fluazinam, benzoxazole, benzo[a]fluoroquinolones, fluazinam hydroxylamine, isopropoxyfenozide, fluindazole, indomethacin, chlorfluazon, pyridabenamide, methylarylpyridinamide, and tetrazolium.

[0195] Preferably, a fungicidal composition is provided comprising a mixture of a crystalline polymorph (form C) of methyl 2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein, and component (C) as an active ingredient, wherein component (B) is a compound selected from the group consisting of: aramalic acid-benzene-S-methyl, cyproconazole, difenoconazole, hexaconazole, prothioconazole, tebuconazole, benzyloxydine, azoxystrobin, oxadiazon, mancozeb, chlorothalonil, fluazinam, fluoxazin, benzoylfluopyram, fluopyram, benzoylfluopyram, fluopyram, methyl arylpyridinamide, and tetrazolium.

[0196] More preferably, a fungicidal composition is provided comprising a mixture of a crystalline polymorph (form C) of methyl 2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein, and component (C) as an active ingredient, wherein component (B) is a compound selected from the group consisting of, or a salt, enantiomer, tautomer, or N-oxide thereof: cycloproconazole, difenoconazole, prothioconazole, tebuconazole, benzyl benzoate, mancozeb, chlorothalonil, and fluopyram.

[0197] Even more preferably, a fungicidal composition is provided comprising a mixture of a crystalline polymorph (form C) of methyl 2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein, and component (C) as an active ingredient, wherein component (B) is a compound selected from the group consisting of, or a salt thereof, enantiomer, tautomer, or N-oxide thereof: difenoconazole, prothioconazole, tebuconazole, benzyl benzoate, and chlorothalonil.

[0198] In another aspect of the invention, a fungicidal composition is provided comprising a mixture of a crystalline polymorph (form C) of methyl 2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein, and a component (B) as an active ingredient, wherein component (B) is a compound selected from the group consisting of: bifenthionil, aramidobenzene, aramidobenzene-S-methyl, copper sulfate, copper hydroxide, copper oxychloride, copper oxide, cyproconazole, difenoconazole, hexaconazole, prothioconazole, propiconazole, tebuconazole, flutriafol, benzyl benzoate, butyl morpholine, azoxystrobin, fenpropathrin, oxadiazon, azoxystrobin, pyraclostrobin, mancozeb, chlorothalonil, fluazinam, fluazinam, fluazinam, pyraclostrobin, pyraclostrobin Amines, fluoxetine, boscalid, fluoxazine, benzovindiflupyr, fluoxetine hydroxylamine, isopropoxypyridine, fluinbazin, indoxacarb, chlorfluazin, pyridazinamide, methyl arylpyridazinamide, tetrazolium, (5R)-3-[3-(3-chloro-2-fluoro-phenoxy)-6-methyl-pyridazin-4-yl]-5-[(2-chloro-4-methyl-phenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine (this compound can be derived from WO4) (This compound can be prepared by the methods described in WO 2020 / 127780 and WO 2021 / 255070), (5S)-3-[3-(3-chloro-2-fluoro-phenoxy)-6-methyl-pyridazin-4-yl]-5-[(2-chloro-4-methyl-phenyl)methyl]-5,6-dihydro-4H-1,2,4-oxadiazine (this compound can be prepared by the methods described in WO 2020 / 127780 and WO 2021 / 255070), ... The following compounds can be prepared by the method described in 2021 / 255070: methyl (Z)-3-methoxy-2-(2-methyl-5-phenyl-phenoxy)prop-2-enoate (this compound can be prepared by the method described in JP 2023078251), ethyl 1-[[4-[[2-(trifluoromethyl)-1,3-dioxolane-2-yl]methoxy]phenyl]methyl]-1H-pyrazole-4-carboxylate (this compound can be prepared by the method described in WO 2021 / 183707), ethyl 1-[[4-[[(1Z)-2-ethoxy-3,3,3-trifluoro-1-propen-1-yl]oxy]phenyl]methyl]-1H-pyrazole-4-carboxylate (this compound can be prepared by the method described in WO 2021 / 183707), 5-[5-(difluoromethyl)-1,3,4-Oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)ethyl]pyrimidin-2-amine (this compound can be prepared by the method described in WO 2021 / 255093), 2-(difluoromethyl)-5-[2-[1-(2,6-difluorophenyl)cyclopropoxy]pyrimidin-5-yl]-1,3,4-oxadiazole (this compound can be prepared by the method described in WO 2021 / 255093), 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2,6-difluorophenyl)cyclopropyl]pyrimidin-2-amine (this compound can be prepared by the method described in WO 2021 / 255093), 2-(difluoromethyl)-5-[2-[1-(2,6-difluorophenyl)cyclopropyl]pyrimidin-2-amine (this compound can be prepared by the method described in WO 2021 / 255093), 2-(difluoromethyl)-5-[2-[1-(2,6-difluorophenyl)cyclopropyl]pyrimidin-2-amine (this compound can be prepared by the method described in WO 2021 / 255093), 2-(difluoromethyl)-5-[2-[1-(2,6-difluorophenyl)cyclopropyl]pyrimidin-2-amine), 2-(difluoromethyl)-5 ... The compounds can be prepared by the methods described in WO 2021 / 255093, such as 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)cyclopropyl]pyrimidin-2-amine (this compound can be prepared by the methods described in WO 2021 / 255093), N-[1-(2-fluorophenyl)cyclopropyl]-5-[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]pyrimidin-2-amine (this compound can be prepared by the methods described in WO 2021 / 255093), and 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(2-fluorophenyl)ethyl]pyrimidin-2-amine (this compound can be prepared by the methods described in WO 2021 / 255093). The following compounds can be prepared by the method described in WO 2021 / 255093: 5-[5-(difluoromethyl)-1,3,4-oxadiazol-2-yl]-N-[1-(3,5-difluorophenyl)ethyl]pyrimidin-2-amine (this compound can be prepared by the method described in WO 2021 / 255093), and N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropaneformamide (this compound can be prepared by WO 2021 / 255093). The following compounds can be prepared by the method described in WO 2017 / 055473: N,2-dimethoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propionamide, or their (R) or (S) enantiomers or mixtures thereof (this compound can be prepared by the method described in WO 2017 / 055473), methyl 3-[(4-chlorophenyl)methyl]-2-hydroxy-1-methyl-2-(1,2,4-triazol-1-ylmethyl)cyclopentanecarboxylate (this compound can be prepared by WO 2017 / 055473). Methyl (2R)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-triazol-1-yl)propionate (this compound can be prepared by the method described in WO2019 / 093522); 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1,2,4-Triazol-1-yl)methyl propionate (this compound can be prepared by the method described in WO 2019 / 093522), 1-[4-(difluoromethoxy)-2-methyl-phenyl]-2-(1,2,4-triazol-1-yl)-1-[1-(trifluoromethyl)cyclopropyl]ethanol (this compound can be prepared by the method described in WO 2019 / 093522), Methyl acetate (prepared by the method described in WO2021 / 249800), (2E)-2-methoxyimino-2-[3-methyl-2-[[(E)-1-[4-(trifluoromethyl)-2-pyridyl]ethyleneamino]oxymethyl]phenyl]acetamide (this compound can be prepared by the method described in WO2022 / 033906), (2E)-2-methoxyimino-N-methyl-2-[3-methyl-2-[[(E)-1-[4-(trifluoromethyl)-2-pyridyl]ethyleneamino]oxymethyl]phenyl]acetamide (this compound can be prepared by the method described in WO2022 / 249800). Methyl acetate (2E)-2-[2-[[(E)-[3-(4-fluorophenyl)-1-methyl-prop-2-ynyne]amino]oxymethyl]-3-methyl-phenyl]-2-methoxyimino-acetate (this compound can be prepared by methods such as those described in WO2021 / 249928), and N-methylacetamide (2E)-2-[2-[[(E)-[3-(4-fluorophenyl)-1-methyl-prop-2-ynyne]amino]oxymethyl]-3-methyl-phenyl]-2-methoxyimino-N-methylacetamide (this compound can be prepared by methods such as those described in WO2021 / 249928). Methyl carbamate (prepared by the method described in WO 2021 / 249928), 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 WO 2020 / 097012), N-[[5-[1-(4-cyclopropyl-2,6-difluoro-phenyl)pyrazol-3-yl]-2-methyl-phenyl]methyl]carbamate (this compound can be prepared by the method described in WO 2020 / 097012), N-[methoxy-[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]butyramide (this compound can be prepared by the method described in WO 2020 / 097012), N-[methoxy-[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]butyramide (this compound can be prepared by the method described in WO 2021 / 249928), N-[methoxy-[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]butyramide (this compound can be prepared by the method described in WO 2020 / 097012 ... The following compounds can be prepared using the methods described in WO 2020 / 256113: 2-methoxy-N-[methoxy-[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]acetamide (this compound can be prepared using the methods described in WO 2020 / 256113) and N-[methoxy-[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]-2-methylpropionamide (this compound can be prepared using the methods described in WO 2020 / 256113).

[0199] Typically, the weight ratio of component (A) to component (B) can be 1000:1 to 1:1000, 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, and 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.

[0200] In one embodiment, a preferred antifungal composition comprising a mixture of components (A) and (B) used in the method of the present invention is disclosed in Tables M1 and M2 below.

[0201] Table M1 - Specific antifungal compositions

[0202]

[0203] Table M2 - Specific fungicidal compositions

[0204]

[0205] The preferred ratio ranges of the preferred compositions used in the methods of the present invention are given in Tables R1 and R2 below. When component (B) is present in an alternative form (e.g., salt / ester), it should be understood that these can be substituted.

[0206] Table R1: Exemplary ratio ranges of specific compositions used in the method of the present invention

[0207]

[0208] Table R2: Exemplary ratio ranges of specific compositions used in the methods of the present invention

[0209]

[0210] In any composition according to the invention, the composition may contain an additional active ingredient component (C), which is different from component (B) and is selected from the group consisting of: bifenthiophanate-methyl, amidophos, copper sulfate, copper hydroxide, chlorpyrifos, aramidoylbenzene, aramidoylbenzene-S-methyl, copper oxychloride, copper oxide, azaconazole, bifenthrin, furazolidone, cyproconazole, difenoconazole, tebuconazole, flutriafol, cyproconazole, fluquinazole, flusilazole, fenbendazole, furazolidone, hexaconazole, imazalil, sulfadiazine, etc. Amiconazole, tebuconazole, fenbendazole, cyproconazole, isoprothiolane, tebuconazole, prothioconazole, pyridaben, imazalil, propiconazole, pyraclostrobin, silflubaconazole, tebuconazole, flufenoxuron, triadimefon, triadimefon, flufenoxuron, cymoxanil, chloropyrimidinol, flufenoxuronol, dodecyl morpholine, benzyl benzoate, butyl morpholine, spirocycline, tridemorpholine, boscalid, carbendazim, methomyl, fluamide, carbendazim, oxychloride, pyraclostrobin, thifluzamide, azoxystrobin, ether amine, tebuconazole, flufenoxuron, ether amine Azoxystrobin, oxadiazon, oxadiazon, azoxystrobin, pyraclostrobin, pyraclostrobin, pyraclostrobin, mancozeb, chlorothalonil, triflupyridamole, oxadiazon, imidacloprid, fluazinam, fluopyram, fluopyram, fluopyram, cyclopyridamole, pyraclostrobin, pyraclostrobin, fluopyram, benzovindiflupyr, fluopyram, isopropoxyl-fluopyram, fluopyram, toluene-pyrazinamide, bifenpyrazinamide, indapoxetine, chlorfluazon, isofentrifluconazole, fluopyram, pyridamole, methyl arylpyridamole Acetamide, isothiazamide, 1-[[4-[[2-(trifluoromethyl)-1,3-dioxolane-2-yl]methoxy]phenyl]methyl]pyrazole-3-carboxylate ethyl ester, 1-[[4-[(Z)-2-ethoxy-3,3,3-trifluoro-prop-1-enoxy]phenyl]methyl]pyrazole-3-carboxylate ethyl ester, N-[[4-[1-(4-cyclopropyl-2,6-difluoro-phenyl)pyrazole-4-yl]-2-methyl-phenyl]methyl]carbamate methyl ester, N-[[4-[1-(2,6-Difluoro-4-isopropyl-phenyl)pyrazol-4-yl]-2-methyl-phenyl]methyl]carbamate, fluopyram, fluopyram, tetrazolium, enoxamethoxy, eugenol, N'-[5-bromo-2-methyl-6-[(1S)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidin, N'-[5-bromo-2-methyl-6-[(1R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidin, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidin, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidin, N'-[5-chloro ...2- [-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methylformamidinium, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methylformamidinium, N'-[5-bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N-methylformamidinium, N-isopropyl-N'-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenyl-ethyl)phenyl]-N-methylformamidinium, N'-[4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-methoxy-2-methyl-benzene] [5-methoxy-2-methyl-4-[(2-trifluoromethyl)oxetane-2-yl]phenyl]-N-methyl-formamidin, N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methyl-formamidin, N-ethyl-N'-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methyl-formamidin, 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, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline, 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4,6-trifluoro-3,3-dimethyl-isoquinoline, 4,4 -Difluoro-3,3-dimethyl-1-(6-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline, 4,4-difluoro-3,3-dimethyl-1-(7-methylpyrazolo[1,5-a]pyridin-3-yl)isoquinoline, 1-(6-chloro-7-methylpyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline, 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 Phosphorus, 4,4-difluoro-1-(5-fluoro-4-methylbenzimidazol-1-yl)-3,3-dimethyl-isoquinoline, 3-(4,4-difluoro-3,3-dimethyl-1-isoquinoline)-7,8-dihydro-6H-cyclopenta[e]benzimidazole, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)prop-2-ol, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)prop-2-ol, 3-[2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxypropyl]imidazol-4-carboxynitrile, 3-[2-(1-chlorocyclopropyl)-3- (3-Chloro-2-fluoro-phenyl)-2-hydroxy-propyl]imidazolium-4-carboxylon, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl ketone, (3-methylisoxazol-5-yl)-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl ketone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetamide, 1-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-thienyl]methyl]pyrazole-4-carboxylic acid ethyl ester, 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]2-thienyl]methyl]pyrazole-4-carboxylic acid ethyl ester, 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, and N-[N-methoxy-C-methyl-carbonimino]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide.

[0211] Component (C) compounds are referred to herein and above by their so-called "ISO common name" or another "common name" or trademark name, as used in individual cases. Component (C) compounds are known and commercially available and / or can be prepared using procedures known in the art.

[0212] In another aspect of the invention, a fungicidal composition is provided comprising a mixture of components (A), (B), and (C) as an active ingredient, wherein component (A) is a crystalline polymorph (form A) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein, and wherein component (B) is the compound difenoconazole or prothioconazole; and wherein component (C) is a compound selected from the group consisting of: cycloproconazole, tebuconazole, benzyl benzoate, mancozeb, chlorothalonil, benzo[a]fluoroquinolones, and fluopyram.

[0213] In another aspect of the invention, a fungicidal composition is provided comprising a mixture of components (A), (B), and (C) as an active ingredient, wherein component (A) is a crystalline polymorph (form B) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein, and wherein component (B) is the compound difenoconazole or prothioconazole; and wherein component (C) is a compound selected from the group consisting of: cycloproconazole, tebuconazole, benzyl benzoate, mancozeb, chlorothalonil, benzo[a]fluoroquinolones, and fluopyram.

[0214] In another aspect of the invention, a fungicidal composition is provided comprising a mixture of components (A), (B), and (C) as an active ingredient, wherein component (A) is a crystalline polymorph (form C) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein, and wherein component (B) is the compound difenoconazole or prothioconazole; and wherein component (C) is a compound selected from the group consisting of: cycloproconazole, tebuconazole, benzyl sulfadiazine, mancozeb, chlorothalonil, benzo[a]fluoroquinolones, and fluopyram.

[0215] In one embodiment of the invention, component (A) is a crystalline polymorph (form A) of methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxy-prop-2-enoate as defined herein, and component (B) is tebuconazole; and

[0216] Component (C) is the compound manganese zinc.

[0217] In one embodiment of the invention, component (A) is a crystalline polymorph (form A) of methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxy-prop-2-enoate as defined herein, and component (B) is tebuconazole; and

[0218] Component (C) is the compound difenoconazole.

[0219] In one embodiment of the invention, component (A) is a crystalline polymorph (form A) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein, and component (B) is the compound benzo[a]fluoroazole; and

[0220] Component (C) is the compound prothioconazole.

[0221] In one embodiment of the invention, component (A) is a crystalline polymorph (form A) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein, and component (B) is the compound benzo[a]fluoroazole; and

[0222] Component (C) is the compound difenoconazole.

[0223] In one embodiment of the invention, component (A) is a crystalline polymorph (form A) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein, and component (B) is the compound prothioconazole; and

[0224] Component (C) is the compound manganese zinc.

[0225] In one embodiment of the invention, component (A) is a crystalline polymorph (form A) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein, and component (B) is the compound prothioconazole; and

[0226] Component (C) is the compound difenoconazole.

[0227] In one embodiment of the invention, component (A) is a crystalline polymorph (form A) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein, and component (B) is the compound prothioconazole; and

[0228] Component (C) is the compound chlorothalonil.

[0229] In one embodiment of the invention, component (A) is a crystalline polymorph (form A) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein, and component (B) is the compound prothioconazole; and

[0230] Component (C) is the compound fluopyram.

[0231] In one embodiment of the invention, component (A) is a crystalline polymorph (form A) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein, and component (B) is manganese zinc; and

[0232] Component (C) is the compound difenoconazole.

[0233] In one embodiment of the invention, component (A) is a crystalline polymorph (form A) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein, and component (B) is the compound difenoconazole; and

[0234] Component (C) is the compound chlorothalonil.

[0235] In one embodiment of the invention, component (A) is a crystalline polymorph (form A) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein, and component (B) is the compound difenoconazole; and

[0236] Component (C) is the compound cyclopropazole.

[0237] In one embodiment of the invention, component (A) is a crystalline polymorph (form B) of methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxy-prop-2-enoate as defined herein, and component (B) is the compound tebuconazole; and

[0238] Component (C) is the compound manganese zinc.

[0239] In one embodiment of the invention, component (A) is a crystalline polymorph (form B) of methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxy-prop-2-enoate as defined herein, and component (B) is the compound tebuconazole; and

[0240] Component (C) is the compound difenoconazole.

[0241] In one embodiment of the invention, component (A) is a crystalline polymorph (form B) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein, and component (B) is the compound benzo[a]fluoroazole; and

[0242] Component (C) is the compound prothioconazole.

[0243] In one embodiment of the invention, component (A) is a crystalline polymorph (form B) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein, and component (B) is the compound benzo[a]fluoroazole; and

[0244] Component (C) is the compound difenoconazole.

[0245] In one embodiment of the invention, component (A) is a crystalline polymorph (form B) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein, and component (B) is the compound prothioconazole; and

[0246] Component (C) is the compound manganese zinc.

[0247] In one embodiment of the invention, component (A) is a crystalline polymorph (form B) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein, and component (B) is the compound prothioconazole; and

[0248] Component (C) is the compound difenoconazole.

[0249] In one embodiment of the invention, component (A) is a crystalline polymorph (form B) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein, and component (B) is the compound prothioconazole; and

[0250] Component (C) is the compound chlorothalonil.

[0251] In one embodiment of the invention, component (A) is a crystalline polymorph (form B) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein, and component (B) is the compound prothioconazole; and

[0252] Component (C) is the compound fluopyram.

[0253] In one embodiment of the invention, component (A) is a crystalline polymorph (form B) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein, and component (B) is manganese zinc; and

[0254] Component (C) is the compound difenoconazole.

[0255] In one embodiment of the invention, component (A) is a crystalline polymorph (form B) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein, and component (B) is the compound difenoconazole; and

[0256] Component (C) is the compound chlorothalonil.

[0257] In one embodiment of the invention, component (A) is a crystalline polymorph (form B) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein, and component (B) is the compound difenoconazole; and

[0258] Component (C) is the compound cyclopropazole.

[0259] In one embodiment of the invention, component (A) is a crystalline polymorph (form C) of methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxy-prop-2-enoate as defined herein, and component (B) is tebuconazole; and

[0260] Component (C) is the compound manganese zinc.

[0261] In one embodiment of the invention, component (A) is a crystalline polymorph (form C) of methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxy-prop-2-enoate as defined herein, and component (B) is tebuconazole; and

[0262] Component (C) is the compound difenoconazole.

[0263] In one embodiment of the invention, component (A) is a crystalline polymorph (form C) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein, and component (B) is the compound benzo[a]fluoroazole; and

[0264] Component (C) is the compound prothioconazole.

[0265] In one embodiment of the invention, component (A) is a crystalline polymorph (form C) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein, and component (B) is the compound benzo[a]fluoroazole; and

[0266] Component (C) is the compound difenoconazole.

[0267] In one embodiment of the invention, component (A) is a crystalline polymorph (form C) of methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxy-prop-2-enoate as defined herein, and component (B) is the compound prothioconazole; and

[0268] Component (C) is the compound manganese zinc.

[0269] In one embodiment of the invention, component (A) is a crystalline polymorph (form C) of methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxy-prop-2-enoate as defined herein, and component (B) is the compound prothioconazole; and

[0270] Component (C) is the compound difenoconazole.

[0271] In one embodiment of the invention, component (A) is a crystalline polymorph (form C) of methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxy-prop-2-enoate as defined herein, and component (B) is the compound prothioconazole; and

[0272] Component (C) is the compound chlorothalonil.

[0273] In one embodiment of the invention, component (A) is a crystalline polymorph (form C) of methyl (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxy-prop-2-enoate as defined herein, and component (B) is the compound prothioconazole; and

[0274] Component (C) is the compound fluopyram.

[0275] In one embodiment of the invention, component (A) is a crystalline polymorph (form C) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein, and component (B) is manganese zinc; and

[0276] Component (C) is the compound difenoconazole.

[0277] In one embodiment of the invention, component (A) is a crystalline polymorph (form C) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein, and component (B) is the compound difenoconazole; and

[0278] Component (C) is the compound chlorothalonil.

[0279] In one embodiment of the invention, component (A) is a crystalline polymorph (form C) of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein, and component (B) is the compound difenoconazole; and

[0280] Component (C) is the compound cyclopropazole.

[0281] Combinations (B) and (C) in combination with component (A) can enhance the latter's antifungal efficacy, and vice versa. Additionally, the antifungal composition is effective against a broader spectrum of fungal pathogens than the individual active ingredients alone can combat.

[0282] Typically, 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. In other respects, 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 should be understood to include both weight-based ratios and molar ratios.

[0283] In embodiments of the present invention, the composition comprises component (A), component (B), and component (C), wherein the weight ratio of component (A) to the sum of components (B) and (C) may 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, and even more preferably 12:1 to 1:25, or 10:1 to 1:20, or 10:1 to 1:10, or 5:1 to 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.

[0284] In one embodiment, a preferred antifungal composition comprising a mixture of components (A), (B), and (C) used in the method of the present invention is disclosed in Tables M3 to M34 below, wherein the term “form A” refers to the crystalline polymorph form A of methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate as defined herein.

[0285] Table M3 - Specific fungicidal compositions

[0286]

[0287] Table M4 - Specific antifungal compositions

[0288]

[0289] Table M5 - Specific fungicidal compositions

[0290]

[0291] Table M6 - Specific antifungal compositions

[0292]

[0293] Table M7 - Specific antifungal compositions

[0294]

[0295] Table M8 - Specific antifungal compositions

[0296]

[0297] Table M9 - Specific fungicidal compositions

[0298]

[0299] Table M10 - Specific fungicidal compositions

[0300]

[0301] Table M11 - Specific antifungal compositions

[0302]

[0303] Table M12 - Specific antifungal compositions

[0304]

[0305] Table M13 - Specific antifungal compositions

[0306]

[0307] Table M14 - Specific antifungal compositions

[0308]

[0309] Table M15 - Specific antifungal compositions

[0310]

[0311] Table M16 - Specific antifungal compositions

[0312]

[0313] Table M17 - Specific antifungal compositions

[0314]

[0315] Table M18 - Specific antifungal compositions

[0316]

[0317] Table M19 - Specific antifungal compositions

[0318]

[0319] Table M20 - Specific fungicidal compositions

[0320]

[0321] Table M21 - Specific antifungal compositions

[0322]

[0323] Table M22 - Specific antifungal compositions

[0324]

[0325] Table M23 - Specific fungicidal compositions

[0326]

[0327] Table M24 - Specific antifungal compositions

[0328]

[0329] Table M25 - Specific fungicidal compositions

[0330]

[0331] Table M26 - Specific antifungal compositions

[0332]

[0333] Table M27 - Specific fungicidal compositions

[0334]

[0335] Table M28 - Specific antifungal compositions

[0336]

[0337] Table M29 - Specific fungicidal compositions

[0338]

[0339] Table M30 - Specific fungicidal compositions

[0340]

[0341] Table M31 - Specific antifungal compositions

[0342]

[0343] Table M32 - Specific fungicidal compositions

[0344]

[0345] Table M33 - Specific fungicidal compositions

[0346]

[0347] Table M34 - Specific antifungal compositions

[0348]

[0349] In a preferred embodiment of the invention, a method is provided for controlling or preventing infection in plants (preferably soybeans) caused by a plant pathogenic fungus (preferably *Dioscorea beanus*), wherein the plant pathogenic fungus comprises an F129L mutation in mitochondrial cytochrome b conferring resistance to a Qo inhibitor. The method comprises applying a fungicidal composition comprising a mixture of components (A) and (B) as active ingredients to the plant, its parts, or the site thereof, wherein the composition is a composition selected from the group consisting of M1.001 to M34.012 (as disclosed in Tables M1 to M34). Preferably, in this embodiment of the invention, the preferred weight ratio of component A:B is as disclosed in Tables R1 and R2.

[0350] Furthermore, according to the present invention, a method for controlling or preventing plant pathogenic fungi, particularly *Cyclocarya paliurus*, on useful plants (preferably soybeans) or their propagation material is provided, the method comprising applying a fungicidal composition to the useful plants, their sites, or their propagation material, wherein the composition is a composition selected from the group consisting of M1.001 to M34.012 (as disclosed in Tables M1 to M34).

[0351] Furthermore, according to the present invention, a method is provided for controlling or preventing plant pathogenic fungi, particularly of the genus *Laminaria* (including *Laminaria sclerotioides* and *Laminaria sacchariformis*), on useful plants (preferably soybeans) or their propagation material, the method comprising applying a fungicidal composition to these useful plants, their sites, or their propagation material, wherein the composition is a composition selected from the group consisting of M1.001 to M34.012 (as disclosed in Tables M1 to M34).

[0352] Furthermore, according to the present invention, a method is provided for controlling or preventing *Phyllostachys beanus* rust on a useful plant (preferably soybean) or its propagation material, wherein the *Phyllostachys beanus* rust comprises at least one of the F120L, Y131F / H, K142R, I145F, or I475T mutations in the CYP51 gene conferring resistance to a sterol demethylation inhibitor (DMI), the method comprising applying a fungicidal composition to the useful plant, its site, or its propagation material, wherein the composition is a composition selected from the group consisting of M1.001 to M34.012 (as disclosed in Tables M1 to M34).

[0353] Furthermore, according to the present invention, a method is provided for controlling or preventing plant pathogenic fungi, particularly those of the genus *Cercospora* (including *Cercospora arachifolia*, *Cercospora beetica*, *Cercospora mustardica*, *Cercospora sugarcane*, *Cercospora flagella*, *Cercospora jansina*, *Cercospora kikuchi*, *Cercospora gourdica*, *Cercospora soybeanica*, *Cercospora sorghumica*, and *Cercospora maize*), on useful plants (preferably soybeans), or on their propagation material, wherein the composition is selected from the group consisting of M1.001 to M34.012 (as disclosed in Tables M1 to M34).

[0354] Furthermore, according to the present invention, a method is provided for controlling or preventing *Cercospora* species (including *Cercospora arachifolia*, *Cercospora beetica*, *Cercospora mustardica*, *Cercospora sugarcane*, *Cercospora flagellata*, *Cercospora jansina*, *Cercospora kikuchi*, *Cercospora gourdica*, *Cercospora soybean*, *Cercospora sorghum*, and *Cercospora maize*) on useful plants (preferably soybeans) or their propagation material, wherein the *Cercospora* species contain a G143A mutation in mitochondrial cytochrome b conferring resistance to Qo inhibitors, the method comprising applying a fungicidal composition to these useful plants, their sites, or their propagation material, wherein the composition is a composition selected from the group consisting of M1.001 to M34.012 (as disclosed in Tables M1 to M34).

[0355] Furthermore, according to the present invention, a method is provided for controlling or preventing *Cercospora* species (including *Cercospora arachifolia*, *Cercospora beetica*, *Cercospora mustardica*, *Cercospora sugarcane*, *Cercospora flagella*, *Cercospora jansina*, *Cercospora kikuchi*, *Cercospora gourdica*, *Cercospora soybean*, *Cercospora sorghum*, and *Cercospora maize*) on useful plants (preferably soybeans) or their propagation material, wherein the *Cercospora* species comprises at least one of the E297K, I330T, or P384S mutations on the CYP51 gene conferring resistance to a sterol demethylation inhibitor (DMI), the method comprising applying a fungicidal composition to these useful plants, their sites, or their propagation material, wherein the composition is a composition selected from the group consisting of M1.001 to M34.012 (as disclosed in Tables M1 to M34).

[0356] Furthermore, according to the present invention, a method is provided for controlling or preventing plant pathogenic fungi, particularly those of the genus *Anthracnose* (including *Anthracnose spores*, *Anthracnose graminearum*, *Anthracnose chrysanthemum*, *Anthracnose florida*, *Anthracnose spheroides*, *Anthracnose spp.*, *Anthracnose graminearum*, *Anthracnose gracilis*, *Anthracnose lentil*, *Anthracnose bean*, *Anthracnose banana*, *Anthracnose cucurbita*, *Anthracnose siamensis*, and *Anthracnose scutellaria*), on useful plants (preferably soybeans) or their propagation material. This method comprises applying a fungicidal composition to these useful plants, their sites, or their propagation material, wherein the composition is selected from the group consisting of M1.001 to M34.012 (as disclosed in Tables M1 to M34).

[0357] Furthermore, according to the present invention, a method is provided for controlling or preventing plant pathogenic fungi, particularly those of the genus *Sclerotium* (including *Sclerotium sclerotium*, *Sclerotium davidii*, and *Sclerotium*), on useful plants (preferably soybeans) or their propagation material, the method comprising applying a fungicidal composition to these useful plants, their sites, or their propagation material, wherein the composition is a composition selected from the group consisting of M1.001 to M34.012 (as disclosed in Tables M1 to M34).

[0358] Furthermore, according to the present invention, a method is provided for controlling or preventing *Sclerotinia sclerotiorum* on a useful plant (preferably soybean) or its propagation material, wherein the *Sclerotinia sclerotiorum* comprises at least one of the following mutations conferring resistance to a succinate dehydrogenase inhibitor (SDHI): H273Y mutation in SDH subunit B, H146R mutation in SDH subunit C, or H132R mutation in SDH subunit D. The method comprises applying a fungicidal composition to these useful plants, their sites, or their propagation material, wherein the composition is a composition selected from the group consisting of M1.001 to M34.012 (as disclosed in Tables M1 to M34).

[0359] Furthermore, according to the present invention, a method is provided for controlling or preventing plant pathogenic fungi, particularly those of the genus *Syngonium* (including *Syngonium celeryensis*, *Syngonium soybeanensis*, and *Syngonium tomatoensis*), on useful plants (preferably soybeans) or their propagation material, the method comprising applying a fungicidal composition to these useful plants, their sites, or their propagation material, wherein the composition is a composition selected from the group consisting of M1.001 to M34.012 (as disclosed in Tables M1 to M34).

[0360] Furthermore, according to the present invention, a method is provided for controlling or preventing plant pathogenic fungi, particularly those of the genus *Peronospora* (including *Peronospora allium*, *Peronospora spinosa*, and *Peronospora peaosa*), on useful plants (preferably soybeans) or their propagation material, the method comprising applying a fungicidal composition to these useful plants, their sites, or their propagation material, wherein the composition is a composition selected from the group consisting of M1.001 to M34.012 (as disclosed in Tables M1 to M34).

[0361] Furthermore, according to the present invention, a method is provided for controlling or preventing plant pathogenic fungi, particularly those of the genus *Metacarpa* (including *Metacarpa alpina*, *Metacarpa hemispherica*, *Metacarpa neovinca*, and *Metacarpa beanica*), on useful plants (preferably soybeans) or their propagation material, the method comprising applying a fungicidal composition to these useful plants, their sites, or their propagation material, wherein the composition is a composition selected from the group consisting of M1.001 to M34.012 (as disclosed in Tables M1 to M34).

[0362] A mixture comprising the polymorph according to the invention and one or more active ingredients as described above can be applied, for example, as a single "ready-to-use" solution, as a combined spray mixture (consisting of separate formulations of these single active ingredient components) (e.g., a "drum mix"), and in combination when applied sequentially (i.e., one after another after a reasonably short period, such as hours or days). The order in which the polymorph according to the invention is applied with one or more active ingredients as described above is not critical for carrying out the invention.

[0363] Favorable application rates are typically 5 g to 2 kg of active ingredient (ai) per hectare (ha), preferably 10 g to 1 kg ai / ha, and most preferably 20 g to 600 g ai / ha. When used as a seed soaking agent, a suitable dosage is 10 mg to 1 g of active substance per kg of seeds.

[0364] When the combination of the present invention is used to treat seeds, a ratio of 0.001 to 50 g of polymorph compound / kg of seed, preferably 0.01 to 10 g / kg of seed, is generally sufficient.

[0365] Appropriately, compositions comprising the polymorphs according to the invention may be applied preventively (meaning before the development of the disease) or therapeutically (meaning after the development of the disease).

[0366] Typically, the formulation comprises, by weight, 0.01% to 90% of an active agent, 0% to 20% of an agriculturally acceptable surfactant, and 10% to 99.99% of a solid or liquid formulation inert agent, as well as one or more adjuvants, wherein the active agent is composed of a polymorph according to the invention, optionally together with other active agents (particularly microbicides or preservatives, etc.). Concentrated forms of the composition typically contain between about 2% and 80%, preferably between about 5% and 70% of the active agent by weight. The formulation may, for example, contain 0.01% to 20%, preferably 0.01% to 5% of the active agent by weight. However, commercial products will preferably be formulated as concentrates, and end users will typically use diluted formulations.

[0367] However, it is preferable to formulate commercial products as concentrates, while end users will typically use diluted formulations.

[0368] Application rates vary widely and depend on soil properties, application method, crop species, pests to be controlled, primary climatic conditions, and other factors governed by application method, application time, and target crop. As a general guideline, compounds can be applied at rates of 1 to 2000 l / ha, particularly 10 to 1000 l / ha.

[0369] Preferred formulations may have the following composition (by weight%):

[0370] Emulsifiable concentrate :

[0371] Active ingredient: 1% to 95%, preferably 60% to 90%

[0372] Surfactant: 1% to 30%, preferably 5% to 20%

[0373] Liquid carrier: 1% to 80%, preferably 1% to 35%

[0374] dust :

[0375] Active ingredient: 0.1% to 10%, preferably 0.1% to 5%

[0376] Solid carrier: 99.9% to 90%, preferably 99.9% to 99%.

[0377] Suspension concentrate:

[0378] Active ingredient: 5% to 75%, preferably 10% to 50%

[0379] Water: 94% to 24%, preferably 88% to 30%

[0380] Surfactant: 1% to 40%, preferably 2% to 30%

[0381] wettable powder :

[0382] Active ingredient: 0.5% to 90%, preferably 1% to 80%

[0383] Surfactant: 0.5% to 20%, preferably 1% to 15%

[0384] Solid carrier: 5% to 95%, preferably 15% to 90%

[0385] Granules:

[0386] Active ingredient: 0.1% to 30%, preferably 0.1% to 15%

[0387] Solid carrier: 99.5% to 70%, preferably 97% to 85%

[0388] The invention will now be described by way of the following non-limiting examples and accompanying drawings, wherein:

[0389] Figure 1 The powder X-ray diffraction pattern of polymorphic form A of the present invention is shown.

[0390] Figure 2 The powder X-ray diffraction pattern of the polymorphic form B of the present invention is shown.

[0391] Figure 3 The predicted powder X-ray diffraction pattern of the polymorphic form C of the present invention is shown.

[0392] Figure 4 The DSC trace of polymorphic form A of the present invention is shown.

[0393] Figure 5 The DSC trace of polymorphic form B of the present invention is shown.

[0394] Figure 6 The predicted ideal solubility of polymorphs A and B of the present invention is shown (as a solubility comparison temperature curve). Example

[0395] 1. Preparation of polymorphs - Form A

[0396] (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate was prepared according to the method described in WO 2022 / 200579.

[0397] The polymorph of the present invention was prepared by adding ethanol to (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate and stirring for at least 30 minutes to ensure dissolution. The sample was then subjected to evaporation crystallization. The obtained crystals were ground using a pestle and mortar, and X-ray diffraction analysis (PXRD) confirmed the presence of polymorph form A of the present invention.

[0398] 2. Preparation of polymorph - Form B

[0399] (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate was prepared according to the method described in WO 2020 / 193387.

[0400] (Z)-2-(5-cyclohexyl-2-methylphenoxy)-3-methoxy-prop-2-enoate was purified by rapid chromatography with ethyl acetate / cyclohexane solution, resulting in crystal nucleation and yielding the polymorph of the present invention. X-ray diffraction (PXRD) analysis confirmed the presence of polymorph B of the present invention.

[0401] 3. Preparation of polymorphs - Form C

[0402] Compounds having formula I were prepared according to the method described in WO 2022 / 200579.

[0403] The polymorph of the present invention was prepared by adding dimethyl carbonate to (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate and stirring for at least 30 minutes to ensure dissolution. The sample was then subjected to evaporation crystallization. The presence of polymorph form C of the present invention was confirmed by single-crystal X-ray diffraction (SCXRD) analysis performed at 100 K (-173°C).

[0404] Analysis of polymorphs

[0405] After preparation using the methods detailed above, these samples were analyzed by powder X-ray diffraction (PXRD) and / or single-crystal X-ray diffraction (SCXRD) and / or differential scanning calorimetry (DSC).

[0406] Powder X-ray diffraction analysis of solid materials was performed at room temperature using a Malvern Panalytical Empyrean powder X-ray diffractometer. The samples were ground for 4 minutes using a marble pestle and mortar, mounted on a zero-background silicon wafer, and the sample surface was leveled using a microscope slide. The pXRD holder was placed in the instrument, rotated (rotation time: 2 seconds), and powder patterns were collected from 3.0° to 40° 2-θ with exposure times of 0.0167° and 23 seconds.

[0407] The powder X-ray diffraction patterns measured for polymorphic forms A and B of the present invention are shown in the figures. Figure 1 and Figure 2 middle.

[0408] Single-crystal intensity data were collected at room temperature and 100 K using a Rigaku SCXRD with a SuperNova (Cu Kα) X-ray source (wavelength: 1.54184 Å) and an Atlas S2 area detector. The data were resolved using the CRYSTALS software package. This data was used to generate the predicted powder X-ray diffraction pattern for the polymorphic form C of this invention. Figure 3 ).

[0409] Differential scanning calorimetry (DSC) was performed using a Waters TA-Discovery DSC 2500. 1–5 mg of sample was weighed into a DSC aluminum crucible, sealed with a sealing cap, and then the sample was analyzed. The temperature profile used for analysis ranged from 25°C to 180°C, with a heating rate of 10°C / min.

[0410] Although the invention has been described with reference to its preferred embodiments and examples, the scope of the invention is not limited to those described embodiments. As will be apparent to those skilled in the art, modifications and rewrites can be made to the above invention without departing from the spirit and scope of the invention, as defined and limited by the appended claims. For all purposes, all publications cited herein are hereby incorporated in their entirety by reference, to the extent that each individual publication is specifically and individually indicated to be so incorporated by reference.

Claims

1. A crystalline polymorph form A of a compound (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester, wherein said polymorph has an X-ray diffraction pattern containing peaks at 12.0° ± 0.2°, 18.6° ± 0.2°, 20.3° ± 0.2° and 22.0° ± 0.2° 2θ, as measured by X-ray diffraction using an X-ray wavelength of 1.5406 Å.

2. The crystalline polymorph according to claim 1, wherein, The polymorph further exhibits peaks at 16.5° ± 0.2°, 18.2° ± 0.2°, 23.5° ± 0.2°, 24.7° ± 0.2° and 26.6° ± 0.2° 2θ.

3. The crystalline polymorph according to claim 2, wherein, The polymorph further exhibits peaks at 14.9° ± 0.2°, 16.9° ± 0.2°, 17.7° ± 0.2°, 21.5° ± 0.2°, 21.8° ± 0.2°, 24.5° ± 0.2° and 27.4° ± 0.2° 2θ.

4. The crystalline polymorph according to any one of claims 1 to 3, wherein, The polymorph exhibits an X-ray diffraction pattern substantially as shown in Figure 1.

5. The crystalline polymorph according to any one of claims 1 to 4, wherein, The polymorph has the following lattice parameters: a = 12.7 Å ± 0.1, b = 11.0 Å ± 0.1, c = 13.1 Å ± 0.1, α = 90.0° ± 0.1°, β = 110.2° ± 0.1°, γ = 90.0° ± 0.1°, and volume = 1706.6 Å. 3 ± 1 Å 3 .

6. A crystalline polymorph form B of a compound (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester, wherein said polymorph has an X-ray diffraction pattern containing peaks at 12.2° ± 0.2°, 18.7° ± 0.2°, 20.4° ± 0.2° and 24.4° ± 0.2° 2θ, as measured by X-ray diffraction using an X-ray wavelength of 1.5406 Å.

7. The crystalline polymorph according to claim 6, wherein, The polymorph further exhibits peaks at 8.4° ± 0.2°, 10.2° ± 0.2°, 18.5° ± 0.2°, 22.1° ± 0.2°, 22.9° ± 0.2°, 23.7° ± 0.2° and 24.9° ± 0.2° 2θ.

8. The crystalline polymorph according to claim 7, wherein, The polymorph further exhibits peaks at 15.9° ± 0.2°, 17.4° ± 0.2°, 18.2° ± 0.2°, 23.3° ± 0.2° and 27.6° ± 0.2° 2θ.

9. The crystalline polymorph according to any one of claims 6 to 8, wherein, The polymorph exhibits an X-ray diffraction pattern that is essentially as shown in Figure 2.

10. A crystalline polymorph form C of a compound (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoic acid methyl ester, wherein said polymorph has an X-ray diffraction pattern containing peaks at 12.1° ± 0.2°, 19.5° ± 0.2°, 20.7° ± 0.2° and 22.3° ± 0.2° 2θ, as measured by X-ray diffraction using an X-ray wavelength of 1.54184 Å.

11. The crystalline polymorph according to claim 10, wherein, The polymorph further exhibits peaks at 8.9° ±0.2°, 16.4° ±0.2°, 17.6° ±0.2°, 18.1° ±0.2°, 21.4° ±0.2°, 24.9° ±0.2° and 25.0° ±0.2° 2θ.

12. The crystalline polymorph according to claim 11, wherein, The polymorph further exhibits peaks at 15.7° ±0.2°, 24.3° ±0.2°, 26.5° ±0.2°, 27.6° ±0.2°, 28.1° ±0.2° 2θ, and 28.6° ±0.2° 2θ.

13. An agricultural chemical composition comprising a polymorph according to any one of claims 1 to 12 and an agriculturally chemically acceptable carrier or diluent, and optionally at least one additional active ingredient.

14. A method for controlling or preventing plant infection by plant pathogenic fungi, wherein a fungicide effective amount of the polymorph of any one of claims 1 to 12, or a composition comprising the polymorph as an active ingredient, is applied to the plant, its parts or the site thereof.

15. The method according to claim 14, wherein, The plant pathogenic fungus contains an F129L mutation in mitochondrial cytochrome b that confers resistance to QoI inhibitors, and the method comprises applying the polymorph of any one of claims 1 to 12, or a composition comprising the polymorph as an active ingredient, to the plant, its parts, or the site thereof.

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