Improved pesticidal compositions

Abstract

This invention relates to compositions comprising methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)- 3-methoxy-prop-2-enoate and certain dispersants, as well as processes to make such compositions.

Description

[0001] Improved Pesticidal Compositions

[0002] The present invention relates to improved pesticidal compositions for controlling or preventing infestation of plants, harvested food crops, seeds or non-living materials by phytopathogenic microorganisms, preferably fungi. More specifically the present invention relates to millbases, or to formulations such as suspension concentrates (SC), suspension-emulsions (SE), flowable suspensions (FS), suspension concentrate-capsule suspension blends (ZC) and water dispersable granules (WG) comprising methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate.

[0003] W02020 / 193387 and WO2021 / 176057 disclose methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)- 3-methoxy-prop-2-enoate and the use thereof for combating phytopathogenic fungi.

[0004] It has been found that certain millbase compositions used in the preparation of aqueous formulations (for example suspension concentrates) can exhibit oversized crystal formation and agglomerates of the active ingredient component. As a result, these defects can lead to sedimentation and viscosity changes that may impact milling operations and also the performance of the final product, for example through the potential blockage of spray nozzles upon spray application. In addition, the presence of oversized particles may result in a partial loss of active ingredient during handling and / or spray application, for example through retention via sedimentation, ultimately leading to a reduced amount of active ingredient being deposited onto the treated plant (or parts therof, or locus thereof). This may affect the bioavailability of the active ingredient on plant surfaces, limit uptake into plant tissues or contact with the target phytopathogenic microorganisms, and ultimately reduce the level and consistency of biological efficacy.

[0005] Therefore, there remains a need for improved liquid formulations containing methyl (Z)-2-(5- cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate which formulations are chemically and physically stable, particularly with regards to improved processability (for example, formulations that are substantially free of oversized crystals and agglomertes after milling and / or formulations that allow a higher concentration of active ingredient without encountering excessive viscosity or overheating during milling), and then upon subsequent dilution that are applicable under typical field conditions whilst maintaining good biological efficacy. In addition, there remains a need for improved liquid formulations which can demonstrate an enhanced and / or prolonged biological efficacy when used in the field. The present invention is aimed at solving some of the problems.

[0006] According to the present invention, there is provided a composition comprising,

[0007] (i) methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate; and

[0008] (ii) a polyoxyalkylene copolymer.

[0009] According to a second aspect of the invention, there is provided a method of controlling or preventing infestation of useful plants by phytopathogenic fungi comprising applying a composition according to the invention, to said plants, to parts thereof or the locus thereof.

[0010] Surprisingly, it has now been found that the addition of a polyoxyalkylene copolymer dispersant to certain compositions comprising methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2- enoate significantly reduces the viscosity level for milling operations and improves the physical stability of the active ingredient component (i.e, eliminates or limits crystallisation, flocculation, aggregation and / or sedimentation) and thus the useful storage life and viability of fungicidal liquid compositions for crop protection applications containing these active ingredients. Furthermore, the addition of a polyoxyalkylene copolymer dispersant may also allow for a higher concentration of active ingredient in the formulation without encountering excessive viscosity or overheating during milling.

[0011] Surprisingly, it has also been found that the compositions as described herein have, for practical purposes, a very advantageous level of biological activity for protecting plants against diseases that are caused by fungi.

[0012] The compositions according to the invention are primarily used as a fungicide. The term “fungicide” as used herein means a compound that controls, modifies, or prevents the growth of fungi. The term “fungicidally effective amount” as used herein means the quantity of such a compound or combination of such compounds that is capable of producing an effect on the growth of fungi. Controlling or modifying effects include all deviation from natural development, such as killing, retardation and the like, and prevention includes barrier or other defensive formation in or on a plant to prevent fungal infection.

[0013] As used herein the term “tank-mix” means that the formulation components or additional active ingredients are mixed in the spray tank at the time of spray application.

[0014] As used herein the term “built-in” refers to formulation components (for example dispersants) that are incorporated into the formulation or formulation concentrate.

[0015] As used herein the term “active ingredient” refers to pesticidal agents that are referred to using their common name, for example, from "The Pesticide Manual", 19th Ed., British Crop Protection Council.

[0016] As used herein the term “anti-foam agent” refers to a chemical additive that reduces and hinders the formation of foam in a composition (including during field application), such as a pesticidal formulation. Anti-foaming agents which may be used in accordance with the present invention include, but are not limited to, polydimethylsiloxanes (eg, XIAMETER™ ACP-1500, Dow, Inc; Antifoam MSA, Univar; Xiameter ACP-0001 , Dow Brasil; Xiameter ACP-0100, Dow Chemical) or a silicone anti-foam emulsion (eg, SAG 1572, Momentive Performance Materials Inc., USA).

[0017] As used herein the term “dispersant or dispersing agent” refers typically to a surfactant substance, which when added to a suspension of solid particles in a liquid better enables the separation of the particles to avoid their settling or clumping together.

[0018] As used herein the term “polyoxyalkylene copolymer” refers to a propylene oxide and ethylene oxide copolymer.

[0019] The polyoxyalkylene copolymer can more preferably be a polyoxyalkylene block copolymer of the AB, ABA, BAB, or ABABA type.

[0020] More particularly, the polyoxyalkylene copolymer can be prepared by ring-opening polymerization of the corresponding cyclic ethylene oxide and propylene oxide monomers.

[0021] Typically, the ring-opening polymerization is initiated by addition of water and alkali hydroxides, such as sodium hydroxide and potassium hydroxide. The block structure of the copolymer is formed by first polymerizing a polymer block using one monomer, before adding a second monomer to form further polymer blocks. In a preferred embodiment, the polyoxyalkylene copolymer can be an ethylene oxide-propylene oxide-ethylene oxide block copolymer (EO-PO-EO block copolymer), or in other words a polyethylene oxide)-poly(propylene oxide)-poly(ethylene oxide) block copolymer or a polyethylene glycol)- poly ropylene glycol)-polyethylene glycol) block copolymer.

[0022] Examples include the GENAPOL® PF series (CLARIANT), the PLURONIC® series (BASF), the SYNPERONIC® PE series (e.g SYNPERONIC® PE / L 62 CRODA), or the TOXIMUL® series (STEPAN).

[0023] In a preferred embodiment, the polyoxyalkylene copolymer is a polyethylene oxide)-poly(propylene oxide)-poly(ethylene oxide) block copolymer.

[0024] Preferably, the polyoxyalkylene copolymer has a molecular weight of from 1 ,000 to 15,000 g / mol, more preferably from 4,000 to 7,000 g / mol, even more preferably from 5,000 g / mol to 6,600 g / mol, and even more preferably still from 5,600 to 6,600 g / mol.

[0025] Preferably, the composition of the invention comprises (ii) a polyoxyalkylene copolymer present at a percentage (%) of from 0.01 % to 30% w / w, preferably from 0.1 % to 15% by w / w, more preferably from 0.5% to 10% w / w, and even more preferably from 0.5% to 5% w / w over the total weight of the composition.

[0026] The skilled person would understand that, the expression “a molecular weight” means an average molecular weight (i.e. a molecular weight approximately of). Molecular weight of a polymer, or in other words the molar mass, can be easily determined by method well-known in the art, such as gel permeation chromatography (GPC).

[0027] When the polyoxyalkylene copolymer is an EO-PO-EO block copolymer, the copolymer can comprise at least 30% (preferably from 30% to 80%) by weight of the polyethylene oxide) block, and preferably at least 40% (preferably from 40% to 60%) by weight of the polyethylene oxide) block, over the total weight of the block copolymer.

[0028] In another preferred embodiment, the polyoxyalkylene copolymer has a poly(propylene oxide) block with a molecular weight of from 900 to 3,500 g / mol, preferably from 1 ,500 g / mol to 3,500 g / mol, and more preferably from 2,000 to 3,300 g / mol.

[0029] As used herein the term “suspension concentrate (SC)” refers to a formulation which is a stable suspension of a solid pesticidal active ingredient compound or mixture of compounds in a liquid, usually intended for dilution with water (in a spray tank or other vessel) before use. The compositions of the present invention may be made up to 100% by weight / weight (w / w) with the addition of water.

[0030] The compositions of the present invention may relate to concentrates designed to be added to a farmer’s spray tank of water or they may be applied directly without further dilution. Alternatively, the compositions of the present invention may relate to suspensions designed to be produced in a farmer’s spray tank of water when a concentrate is mixed with water in the spray tank.

[0031] In another object of the present invention, the compositions can be used to prepare a suspension concentrate (SC); a suspension-emulsion (SE); a flowable suspension (FS); a suspension concentratecapsule suspension blend (ZC); a capsule suspension (CS) or a water dispersable granule (WG). More preferably, suspension concentrate (SC) or a suspension-emulsion (SE). More preferably, a suspension concentrate (SC).

[0032] Preferably, the composition of the invention is an aqueous composition.

[0033] In one embodiment, the composition of the invention is a suspension concentrate (SC). Preferably, in the composition of the invention the compound (i) methyl (Z)-2-(5-cyclohexyl-2-methyl- phenoxy)-3-methoxy-prop-2-enoate is present at a percentage (%) of from 0.01 % to 70% w / w (weight / weight) of the total composition. More preferably of from about 1 % to 60% w / w (weight / weight) of the total composition. Even more preferably, from about 3% to 55% w / w of the total composition. Even more preferably still, from about 5% to 45% w / w of the total composition.

[0034] Preferably, the composition of the invention comprises (iii) an acrylic graft copolymer. More preferably, the composition comprises from 0.0005% to 30% w / w of the acrylic graft copolymer, preferably from 0.01 % to 20% by w / w of the acrylic graft copolymer, more preferably from 0.1 % to 10% w / w of the acrylic graft copolymer, even more preferably from 1 % to 5% w / w of the acrylic graft copolymer over the total weight of the composition.

[0035] The acrylic graft copolymer typically has a comb- or star-like structure, and preferably a comb-like structure.

[0036] Graft copolymers are branched copolymers wherein the components forming the side chains are structurally different from the components forming the main chain.

[0037] Comb-like polymers comprise of a main chain (backbone) which contains branch points from each of which a linear side chain emanates.

[0038] Star-like polymers comprise of a multifunctional centre from which at least three polymer chains radiate.

[0039] In a preferred embodiment, the acrylic graft copolymer can be an amphipathic copolymer.

[0040] More particularly, the acrylic graft copolymer comprises at least one component A, which is solvated by an aqueous medium (hydrophilic part), and at least one other component B which is hydrophobic.

[0041] Suitable acrylic graft copolymers may comprise polyethylene glycol, mono-methyl ethers of polyethylene glycol, poly(vinyl pyrrolidone), poly(acrylamide) or poly(vinyl alcohol) as hydrophilic side chain, while the hydrophobic backbone may comprise polymers and copolymers of styrene, methyl acrylate, methyl methacrylate, ethyl acrylate, 2-ethylhexyl acrylate, lauryl methacrylate, or vinyl acetate. Such acrylic graft copolymers can for example be prepared by converting the mono-methyl ether of a polyethylene glycol to the acrylic or methacrylic ester, which is then subjected to radical polymerization with other unsaturated monomers such as styrene, ethyl acrylate, or methyl methacrylate. It is also possible to prepare such acrylic graft copolymers by reacting a hydrophobic polymer backbone, which consists chemically reactive sites such as carboxyl, hydroxy, or amine groups, with monomeric alkylene oxides, such as ethylene oxide and propylene oxide, to form hydrophilic side chains.

[0042] More preferably, the acrylic graft copolymer is a non-ionic polymer, and more particularly with a comb-like structure.

[0043] In the present invention, the acrylic graft copolymer can comprise polyethylene glycol and / or mono-ether polyethylene glycol side chains.

[0044] The acrylic graft copolymer can also comprise a backbone obtained from acrylate and / or methacrylate monomers.

[0045] Preferably, the composition comprises (iii) an acrylic graft copolymer comprising a backbone obtained from acrylate and / or methacrylate monomers, and side chains comprising polyethylene glycol and / or mono-ether polyethylene glycol, giving more particularly the polymer a comb-like structure. Preferably, the composition of the invention comprises (iii) an acrylic graft copolymer having an an HLB (Hydrophilic-lipophilic balance) value of from 10 to 13. More preferably 12.

[0046] For example, the acrylic graft copolymer of the present invention can be Atlox 4913™ supplied by CRODA, or Tersperse 2500™ supplied by HUNTSMAN.

[0047] Preferably, the composition of the invention comprises (iv) at least one sulfonate and / or sulfate. Such sulfonate and sulfates (dispersing and / or wetting agents ) include, but are not limited to, lignosulfonate salts (e.g, Ufoxane 3A, Borregard AS; Borresperse NA, Borregard AS; Polyfon™ H, Reax® 100M, Ingevity; Marasperse CBOS-4 powder, LignoTech), alkyl or polyalkyl naphthalene sulfonate salts (e.g Supragil®WP, Supragil®MNS / 90, Agnique®ANS 4DNP, Agnique®ANS 3DNP-U), naphthalene sulfonate salts condensed with formaldehyde (e.g, Morwet D-425, Nouryon Surface Chemistry AB, Sweden. CAS no.: 9084-06-4 ((CioHsOaS'C^C^n’xNa)), Tersperse® 2020 from Indorama, Tamol®N &NN grades from BASF), phenol sulfonate salts condensed with formaldehyde (e.g Tamol® PP, DN range available from BASF), cresol sulfonates salts condensed with formaldehyde (Dispersogen™ 1494 liq available from Clariant), alkylbenzene sulfonate salts (eg, Rhodacal® DS-10 available from Syensqo), aryl sulfates, alkyl or polyalkyl aryl sulfates (for example, but not limited to, tristyrylphenol sulfate) and alkyl sulfates (for example, but not limited to, sodium lauryl sulfate).

[0048] Preferably, the composition comprises (iv) at least one sulfonate and / or sulfate selected from the group consisting of lignosulfonates, aryl sulfonates, alkyl or polyalkyl aryl sulfonates, alkyl sulfonates, aryl sulfates, alkyl or polyalkyl aryl sulfates (for example, but not limited to, tristyrylphenol sulfate) and alkyl sulfates (for example, but not limited to, sodium lauryl sulfate). More preferably the composition comprises (iv) at least one sulfonate and / or sulfate selected from the group consisting of lignosulfonates, aryl sulfonates, alkyl or polyalkyl aryl sulfonates, alkyl sulfonates, aryl sulfates, alkyl or polyalkyl aryl sulfates (for example, but not limited to, tristyrylphenol sulfate) and alkyl sulfates (for example, but not limited to, sodium lauryl sulfate) and wherein the sulfonate and / or sulfate is an amine salt. More preferably, the composition comprises (iv) at least one sulfonate and / or sulfate selected from the group consisting of triethanolamine C10-13-alkyl benzenesulfonic acid and tristyryl phenol sulfate ammomium salt. Even more preferably, the the composition comprises (iv) triethanolamine dodecylbenzenesulfonate.

[0049] Preferably, the composition of the invention comprises (iv) at least one sulfonate and / or sulfate present at a percentage of from about 0.1 % to 30% w / w (weight / weight) of the total composition. More preferably, from about 0.1 % to 15% w / w of the total composition. More preferably, from about 0.5 % to 10% w / w of the total composition. Even more preferably, from about 0.5% to 5% w / w of the total composition. Even more preferably still, from about 0.5% to 3% w / w of the total composition.

[0050] Preferably, the composition of the present invention further comprises (v) one or more further pesticides selected from the group consisting of: bixafen, fenpyrazamine, copper sulfate, copper hydroxide, triclopyricarb, acibenzolar, acibenzolar-S- methyl, copper oxychloride, copper oxide, azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, furametpyr, hexaconazole, imazalil, imibenconazole, ipconazole, metconazole, myclobutanil, pefurazoate, penconazole, prothioconazole, pyrifenox, prochloraz, propiconazole, pyrisoxazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triflumizole, triticonazole, fenarimol, nuarimol, dodemorph, fenpropidin, fenpropimorph, spiroxamine, tridemorph, boscalid, carboxin, fenfuram, flutolanil, mepronil, oxycarboxin, penthiopyrad, thifluzamide, azoxystrobin, bifemetstrobin, dimoxystrobin, fenaminstrobin, flufenoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, trifloxystrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, mancozeb, chlorothalonil, cyclobutrifluram, famoxadone, fenamidone, fluazinam, fluoxytioconazole, fluxapyroxad, fenhexamid, pyribencarb, triforine, isopyrazam, sedaxane, benzovindiflupyr, pydiflumetofen, isoflucypram, fluindapyr, mandestrobin, pyraziflumid, inpyrfluxam, mefentrifluconazole, ipfentrifluconazole, penflufen, florylpicoxamid, metarylpicoxamid, isofetamid, ethyl 1 -[[4- [[2- (triflu o romethy I)- 1 ,3-dioxolan-2-yl]methoxy]phenyl]methyl]pyrazole-3-carboxylate, ethyl 1 -[[4- [(Z)-2-ethoxy-3,3,3-trifluoro-prop-1 -enoxy]phenyl]methyl]pyrazole-3-carboxylate, methyl N-[[4-[1 -(4- cyclopropyl-2,6-difluoro-phenyl)pyrazol-4-yl]-2-methyl-phenyl]methyl]carbamate, methyl N-[[4-[1-(2,6- difluoro-4-isopropyl-phenyl)pyrazol-4-yl]-2-methyl-phenyl]methyl]carbamate, fluopyram, flufenoxadiazam, metyltetraprole, enoxastrobin, coumoxystrobin, (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, (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, 2-tert-butyl-4-(3-chloro-2-fluoro-phenoxy)-N-[2-(2,4-dimethylphenyl)-2,2- difluoro-ethyl]pyrazole-3-carboxamide, methyl (2R)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy- 3-(1 ,2,4-triazol-1-yl)propanoate, methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1 ,2,4- triazol-1-yl)propanoate, N'-[5-bromo-2-methyl-6-[(1 S)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N- methyl-formamidine, N'-[5-bromo-2-methyl-6-[(1 R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N- methyl-formamidine, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl- formamidine, N'-[5-chloro-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl- formamidine, N'-[5-bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methyl- formamidine, N'-[5-bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N- isopropyl-N’-[5-methoxy-2-methyl-4-(2, 2, 2-trifluoro-1 -hydroxy-1 -phenyl-ethyl)phenyl]-N-methyl- formamidine, N’-[4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-methoxy-2-methyl-phenyl]-N- isopropyl-N-methyl-formamidine, N-ethyl-N’-[5-methoxy-2-methyl-4-[(2-trifluoromethyl)oxetan-2- yl]phenyl]-N-methyl-formamidine, N-ethyl-N’-[5-methoxy-2-methyl-4-[(2-trifuoromethyl)tetrahydrofuran-

[0051] 2-yl]phenyl]-N-methyl-formamidine, N-[(1 R)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-

[0052] 3-carboxamide, N-[(1 S)-1-benzyl-3-chloro-1-methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide, N-

[0053] [(1 R)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8-fluoro-quinoline-3-carboxamide, N-[(1 S)-1-benzyl- 3 , 3 , 3-trifl uoro- 1 -methyl-propyl]-8-fluoro-quinoline-3-carboxamide, N-[(1 R)-1 -benzyl- 1 ,3-dimethyl-butyl]- 7,8-difluoro-quinoline-3-carboxamide, N-[(1 S)-1 -benzyl- 1 ,3-dimethyl-butyl]-7,8-difluoro-quinoline-3- carboxamide, 8-fluoro-N-[(1 R)-1-[(3-fluorophenyl)methyl]-1 ,3-dimethyl-butyl]quinoline-3-carboxamide, 8-fluoro-N-[(1 S)-1 -[(3-fluorophenyl)methyl]-1 ,3-dimethyl-butyl]quinoline-3-carboxamide, N-[(1 R)-1 - benzyl-1 ,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide, N-[(1 S)-1 -benzyl- 1 ,3-dimethyl-butyl]-8- fluoro-quinoline-3-carboxamide, N-((1 R)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro-quinoline-3- carboxamide, N-((1 S)-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-methyl-pyrazolo[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, 4,4-difluoro-1-(5-fluoro-4-methyl-benzimidazol-1-yl)-3,3- dimethyl-isoquinoline, 3-(4,4-difluoro-3,3-dimethyl-1-isoquinolyl)-7,8-dihydro-6H- cyclopenta[e]benzimidazole, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1 ,2,4-triazol-1- yl)propan-2-ol, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1 -(1 , 2 ,4-tri azo I- 1 -yl)propan-2-ol, 3- [2-(1-chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile, 3-[2-(1- chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile, (5-methyl-2- pyridyl)-[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]phenyl]methanone, (3-methylisoxazol-5-yl)-[4-[5- (trifluoromethyl)-l ,2,4-oxadiazol-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1 ,2,4- oxadiazol-3-yl]phenyl]acetamide, ethyl 1-[[5-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]-2- thienyl]methyl]pyrazole-4-carboxylate, 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-carbonimidoyl]-4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]benzamide.

[0054] More preferably, the composition of the present invention further comprises (v) one or more further pesticides selected from the group consisting of: bixafen, acibenzolar, acibenzolar-S-methyl, copper sulfate, copper hydroxide, copper oxychloride, copper oxide, cyproconazole, difenoconazole, hexaconazole, prothioconazole, propiconazole, tebuconazole, epoxiconazole, fenpropidin, fenpropimorph, azoxystrobin, bifemetstrobin, dimoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, mancozeb, chlorothalonil, fluazinam, fluxapyroxad, isopyrazam, sedaxane, boscalid, flufenoxadiazam, benzovindiflupyr, pydiflumetofen, isoflucypram, fluindapyr, inpyrfluxam, mefentrifluconazole, florylpicoxamid, metarylpicoxamid, metyltetraprole, (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, (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, 2-tert-butyl-4-(3-chloro-2-fluoro-phenoxy)-N-[2-(2,4- dimethylphenyl)-2,2-difluoro-ethyl]pyrazole-3-carboxamide, methyl (2R)-2-[2-chloro-4-(4- chlorophenoxy)phenyl]-2-hydroxy-3-(1 ,2,4-triazol-1-yl)propanoate and methyl 2-[2-chloro-4-(4- chlorophenoxy)phenyl]-2-hydroxy-3-(1 ,2,4-triazol-1-yl)propanoate. Even more preferably, the composition of the present invention further comprises (v) one or more further pesticides selected from the group consisting of cyproconazole, difenoconazole, hexaconazole, prothioconazole, propiconazole, tebuconazole, epoxiconazole, fenpropidin, fenpropimorph, mancozeb, chlorothalonil, fluazinam, fluxapyroxad, isopyrazam, flufenoxadiazam, benzovindiflupyr, pydiflumetofen, isoflucypram, fluindapyr, inpyrfluxam, mefentrifluconazole, florylpicoxamid, metarylpicoxamid and metyltetraprole. Even more preferably still, the composition of the present invention further comprises (v) one or more further pesticides (preferably one or two) selected from the group consisting of cyproconazole, difenoconazole, hexaconazole, prothioconazole, propiconazole, tebuconazole, mancozeb, chlorothalonil, benzovindiflupyr and pydiflumetofen. Yet even more preferably still, the composition of the present invention further comprises (v) one or more further pesticides (preferably one or two) selected from the group consisting of prothioconazole, mancozeb and pydiflumetofen. Most preferably, the composition of the present invention further comprises (v) prothioconazole.

[0055] In another embodiment, the composition of the present invention further comprises (v) prothioconazole and pydiflumetofen.

[0056] In another embodiment, the composition of the present invention further comprises (v) prothioconazole and mancozeb.

[0057] In another embodiment, the composition of the present invention further comprises (v) pydiflumetofen and mancozeb.

[0058] Preferably, the further compound (v) is present at a percentage (%) of from 0.01 % to 70% w / w (weight / weight) of the total composition. More preferably of from about 1 % to 50% w / w (weight / weight) of the total composition. Even more preferably, from about 3% to 45% w / w of the total composition. Even more preferably still, from about 5% to 40% w / w of the total composition.

[0059] The compositions of the present invention may include other ingredients such as a surfactant, an emulsifier, a solvent, a polymer, an anti-foam agent, an anti-bacterial agent, a colourant and a perfume, which are well known to the man skilled in the art. Standard formulation publications disclose such formulation components suitable for use with the present invention (for example, Chemistry and Technology of Agrochemical Formulations, Ed. Alan Knowles, published by Kluwer Academic Publishers, The Netherlands in 1998; and Adjuvants and Additives: 2006 Edition by Alan Knowles, Agrow Report DS256, published by Informa UK Ltd, December 2006). The compositions may also comprise other ingredients for improving formulation compatibility; such as hydrotropes and viscosity reducing aids, as discussed in WO2012 / 052545, which may be suitable for use with the composition of the present invention.

[0060] Preferably, the compositions of the invention further comprise (vi) an anti-foam agent. More preferably, the anti-foam agent is polydimethylsiloxane.

[0061] Preferably, the anti-foam agent (vi) is present at a percentage (%) of from 0.001 % to 10 % w / w, preferably from about 0.01 % to about 5% w / w, more preferably from about 0.1 % to about 1 % w / w of the total composition.

[0062] Typically, in the compositions of the invention each additional formulation ingredient will be present at a percentage (%) of from 0.001 % to 15 % w / w, preferably from about 0.01 % to about 10% w / w, more preferably from about 0.01 % to about 6% w / w of the total composition.

[0063] Preferably, the compositions according to the invention comprise from 1 to 10% w / w of 1 ,2- propylene glycol of the total composition, and more preferably, from 2 to 8% w / w of 1 ,2-propylene glycol of the total composition.

[0064] Preferably, the compositions according to the invention comprise 0.001 to 10% w / w of a thickening agent of the total composition, which may be selected from a natural gum substance, such as guar gum or xanthan gum, or a montmorillonite-type clay (eg, Bentopharm™ 20, Wilfrid Smith, UK).

[0065] Suitable agricultural carriers that are useful in formulating the compositions of the invention in the formulation types described above are well known to those skilled in the art.

[0066] Suitable solid carriers include, for example, talc, titanium dioxide, pyrophyllite clay, silica, attapulgite clay, kieselguhr, chalk, diatomaxeous earth, lime, calcium carbonate, bentonite clay, fuller’s earth, cotton seed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour and lignin. In addition, other further biocidally active ingredients or compositions may be combined with the compositions of the invention and used in the methods of the invention and applied simultaneously or sequentially with the compositions of the invention. When applied simultaneously, these further active ingredients may be formulated together with the compositions of the invention or mixed in, for example, the spray tank. These further biocidally active ingredients may be fungicides, herbicides, insecticides, bactericides, acaricides, nematicides and / or plant growth regulators.

[0067] Pesticidal agents are referred to herein using their common name are known, for example, from "The Pesticide Manual", 15th Ed., British Crop Protection Council 2009.

[0068] In addition, the compositions of the invention may also be applied with one or more systemically acquired resistance inducers (“SAR” inducer). SAR inducers are known and described in, for example, United States Patent No. US 6,919,298 and include, for example, salicylates and the commercial SAR inducer acibenzolar-S-methyl.

[0069] In a preferred embodiment there is provided a composition (preferably an aqueous composition) comprising,

[0070] (i) methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate; and

[0071] (ii) a polyoxyalkylene copolymer; and

[0072] (iii) an acrylic graft copolymer.

[0073] More preferably, there is provided a composition (preferably an aqueous composition) comprising,

[0074] (i) methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate;

[0075] (ii) a polyethylene oxide)-poly(propylene oxide)-poly(ethylene oxide) block copolymer; and

[0076] (iii) an acrylic graft copolymer comprising a backbone obtained from acrylate and / or methacrylate monomers, and side chains comprising polyethylene glycol and / or mono-ether polyethylene glycol.

[0077] Even more preferably, there is provided an aqueous composition comprising,

[0078] (i) methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate (preferably present at a percentage (%) of from 0.01 % to 70% w / w (weight / weight) of the total composition, more preferably of from about 1 % to 60% w / w (weight / weight) of the total composition, even more preferably, from about 3% to 55% w / w of the total composition, even more preferably still, from about 5% to 45% w / w of the total composition);

[0079] (ii) a polyethylene oxide)-poly(propylene oxide)-poly(ethylene oxide) block copolymer having a molecular weight of from 4,000 to 7,000 g / mol (preferably, present at a percentage (%) of from 0.01 % to 30% w / w, preferably from 0.1 % to 15% by w / w, and more preferably from 0.5% to 5% w / w, over the total weight of the composition); and

[0080] (iii) an acrylic graft copolymer comprising a backbone obtained from acrylate and / or methacrylate monomers, and side chains comprising polyethylene glycol and / or mono-ether polyethylene glycol ( preferably, present at a percentage (%) of from 0.0005% to 30% w / w, more preferably from 0.01 % to 20% by w / w, and even more preferably from 0.1 % to 10% w / w, over the total weight of the composition).

[0081] Even more preferably still, there is provided an aqueous composition comprising, (i) methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate (preferably present at a percentage (%) of from 0.01 % to 70% w / w (weight / weight) of the total composition, more preferably of from about 1 % to 60% w / w (weight / weight) of the total composition, even more preferably, from about 3% to 55% w / w of the total composition, even more preferably still, from about 5% to 45% w / w of the total composition);

[0082] (ii) a polyethylene oxide)-poly(propylene oxide)-poly(ethylene oxide) block copolymer having a molecular weight of from 5,000 g / mol to 6,600 g / mol (preferably, present at a percentage (%) of from 0.01 % to 30% w / w, preferably from 0.1 % to 15% by w / w, and more preferably from 0.5% to 5% w / w, over the total weight of the composition); and

[0083] (iii) an acrylic graft copolymer comprising a backbone obtained from acrylate and / or methacrylate monomers, and side chains comprising polyethylene glycol and / or mono-ether polyethylene glycol ( preferably, present at a percentage (%) of from 0.0005% to 30% w / w, more preferably from 0.01 % to 20% by w / w, and even more preferably from 0.1 % to 10% w / w, over the total weight of the composition).

[0084] In another embodiment, there is provided a composition (preferably an aqueous composition) comprising,

[0085] (i) methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate; and

[0086] (ii) a polyoxyalkylene copolymer;

[0087] (iii) an acrylic graft copolymer; and

[0088] (iv) at least one sulfonate and / or sulfate.

[0089] Preferably, there is provided a composition (preferably an aqueous composition) comprising,

[0090] (i) methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate;

[0091] (ii) a polyethylene oxide)-poly(propylene oxide)-poly(ethylene oxide) block copolymer;

[0092] (iii) an acrylic graft copolymer comprising a backbone obtained from acrylate and / or methacrylate monomers, and side chains comprising polyethylene glycol and / or mono-ether polyethylene glycol; and

[0093] (iv) at least one sulfonate and / or sulfate selected from the group consisting of lignosulfonates, aryl sulfonates, alkyl or polyalkyl aryl sulfonates, alkyl sulfonates, aryl sulfates, alkyl or polyalkyl aryl sulfates (for example, but not limited to, tristyrylphenol sulfate) and alkyl sulfates (for example, but not limited to, sodium lauryl sulfate).

[0094] More preferably, there is provided an aqueous composition comprising,

[0095] (i) methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate (preferably present at a percentage (%) of from 0.01 % to 70% w / w (weight / weight) of the total composition, more preferably of from about 1 % to 60% w / w (weight / weight) of the total composition, even more preferably, from about 3% to 55% w / w of the total composition, even more preferably still, from about 5% to 45% w / w of the total composition);

[0096] (ii) a polyethylene oxide)-poly(propylene oxide)-poly(ethylene oxide) block copolymer having a molecular weight of from 4,000 to 7,000 g / mol (preferably, present at a percentage (%) of from 0.01 % to 30% w / w, preferably from 0.1 % to 15% by w / w, and more preferably from 0.5% to 5% w / w, over the total weight of the composition); (iii) an acrylic graft copolymer comprising a backbone obtained from acrylate and / or methacrylate monomers, and side chains comprising polyethylene glycol and / or mono-ether polyethylene glycol ( preferably, present at a percentage (%) of from 0.0005% to 30% w / w, more preferably from 0.01 % to 20% by w / w, and even more preferably from 0.1 % to 10% w / w, over the total weight of the composition); and

[0097] (iv) at least one sulfonate and / or sulfate selected from the group consisting of lignosulfonates, aryl sulfonates, alkyl or polyalkyl aryl sulfonates, alkyl sulfonates, aryl sulfates, alkyl or polyalkyl aryl sulfates and alkyl sulfates and wherein the sulfonate and / or sulfate is an amine salt (preferably, present at a percentage of from about 0.1 % to 30% w / w (weight / weight) of the total composition, more preferably, from about 0.1 % to 15% w / w of the total composition, more preferably, from about 0.5 % to 10% w / w of the total composition, even more preferably, from about 0.5% to 5% w / w of the total composition, even more preferably still, from about 0.5% to 3% w / w of the total composition).

[0098] Even more preferably, there is provided an aqueous composition comprising,

[0099] (i) methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate (preferably present at a percentage (%) of from 0.01 % to 70% w / w (weight / weight) of the total composition, more preferably of from about 1 % to 60% w / w (weight / weight) of the total composition, even more preferably, from about 3% to 55% w / w of the total composition, even more preferably still, from about 5% to 45% w / w of the total composition);

[0100] (ii) a polyethylene oxide)-poly(propylene oxide)-poly(ethylene oxide) block copolymer having a molecular weight of from 5,000 g / mol to 6,600 g / mol (preferably, present at a percentage (%) of from 0.01 % to 30% w / w, preferably from 0.1 % to 15% by w / w, and more preferably from 0.5% to 5% w / w, over the total weight of the composition);

[0101] (iii) an acrylic graft copolymer comprising a backbone obtained from acrylate and / or methacrylate monomers, and side chains comprising polyethylene glycol and / or mono-ether polyethylene glycol ( preferably, present at a percentage (%) of from 0.0005% to 30% w / w, more preferably from 0.01 % to 20% by w / w, and even more preferably from 0.1 % to 10% w / w, over the total weight of the composition); and

[0102] (iv) at least one sulfonate and / or sulfate selected from the group consisting of triethanolamine C10-13- alkyl benzenesulfonic acid and tristyryl phenol sulfate ammomium salt (more preferably, triethanolamine dodecylbenzenesulfonate) (preferably, present at a percentage of from about 0.1 % to 30% w / w (weight / weight) of the total composition, more preferably, from about 0.1 % to 15% w / w of the total composition, more preferably, from about 0.5 % to 10% w / w of the total composition, even more preferably, from about 0.5% to 5% w / w of the total composition, even more preferably still, from about 0.5% to 3% w / w of the total composition).

[0103] In another embodiment, there is provided a composition (preferably an aqueous composition) comprising,

[0104] (i) methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate; and

[0105] (ii) a polyoxyalkylene copolymer;

[0106] (iii) an acrylic graft copolymer; (iv) at least one sulfonate and / or sulfate; and

[0107] (v) one or more further pesticides selected from the group consisting of: bixafen, acibenzolar, acibenzolar-S-methyl, copper sulfate, copper hydroxide, copper oxychloride, copper oxide, cyproconazole, difenoconazole, hexaconazole, prothioconazole, propiconazole, tebuconazole, epoxiconazole, fenpropidin, fenpropimorph, azoxystrobin, bifemetstrobin, dimoxystrobin, trifloxystrobin, picoxystrobin, pyraclostrobin, mancozeb, chlorothalonil, fluazinam, fluxapyroxad, isopyrazam, sedaxane, boscalid, flufenoxadiazam, benzovindiflupyr, pydiflumetofen, isoflucypram, fluindapyr, inpyrfluxam, mefentrifluconazole, florylpicoxamid, metarylpicoxamid, metyltetraprole, (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, (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, 2-tert-butyl-4-(3-chloro-2-fluoro-phenoxy)-N-[2-(2,4- dimethylphenyl)-2,2-difluoro-ethyl]pyrazole-3-carboxamide, methyl (2R)-2-[2-chloro-4-(4- chlorophenoxy)phenyl]-2-hydroxy-3-(1 ,2,4-triazol-1-yl)propanoate and methyl 2-[2-chloro-4-(4- chlorophenoxy)phenyl]-2-hydroxy-3-(1 ,2,4-triazol-1-yl)propanoate.

[0108] Preferably, there is provided a composition (preferably an aqueous composition) comprising,

[0109] (i) methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate;

[0110] (ii) a polyethylene oxide)-poly(propylene oxide)-poly(ethylene oxide) block copolymer;

[0111] (iii) an acrylic graft copolymer comprising a backbone obtained from acrylate and / or methacrylate monomers, and side chains comprising polyethylene glycol and / or mono-ether polyethylene glycol;

[0112] (iv) at least one sulfonate and / or sulfate selected from the group consisting of lignosulfonates, aryl sulfonates, alkyl or polyalkyl aryl sulfonates, alkyl sulfonates, aryl sulfates, alkyl or polyalkyl aryl sulfates (for example, but not limited to, tristyrylphenol sulfate) and alkyl sulfates (for example, but not limited to, sodium lauryl sulfate); and

[0113] (v) one or more further pesticides selected from the group consisting of cyproconazole, difenoconazole, hexaconazole, prothioconazole, propiconazole, tebuconazole, epoxiconazole, fenpropidin, fenpropimorph, mancozeb, chlorothalonil, fluazinam, fluxapyroxad, isopyrazam, flufenoxadiazam, benzovindiflupyr, pydiflumetofen, isoflucypram, fluindapyr, inpyrfluxam, mefentrifluconazole, florylpicoxamid, metarylpicoxamid and metyltetraprole.

[0114] More preferably, there is provided an aqeuous composition comprising,

[0115] (i) methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate (preferably present at a percentage (%) of from 0.01 % to 70% w / w (weight / weight) of the total composition, more preferably of from about 1 % to 60% w / w (weight / weight) of the total composition, even more preferably, from about 3% to 55% w / w of the total composition, even more preferably still, from about 5% to 45% w / w of the total composition);

[0116] (ii) a polyethylene oxide)-poly(propylene oxide)-poly(ethylene oxide) block copolymer having a molecular weight of from 4,000 to 7,000 g / mol (preferably, present at a percentage (%) of from 0.01 % to 30% w / w, preferably from 0.1 % to 15% by w / w, and more preferably from 0.5% to 5% w / w, over the total weight of the composition); (iii) an acrylic graft copolymer comprising a backbone obtained from acrylate and / or methacrylate monomers, and side chains comprising polyethylene glycol and / or mono-ether polyethylene glycol ( preferably, present at a percentage (%) of from 0.0005% to 30% w / w, more preferably from 0.01 % to 20% by w / w, and even more preferably from 0.1 % to 10% w / w, over the total weight of the composition);

[0117] (iv) at least one sulfonate and / or sulfate selected from the group consisting of lignosulfonates, aryl sulfonates, alkyl or polyalkyl aryl sulfonates, alkyl sulfonates, aryl sulfates, alkyl or polyalkyl aryl sulfates and alkyl sulfates and wherein the sulfonate and / or sulfate is an amine salt (preferably, present at a percentage of from about 0.1 % to 30% w / w (weight / weight) of the total composition, more preferably, from about 0.1 % to 15% w / w of the total composition, more preferably, from about 0.5 % to 10% w / w of the total composition, even more preferably, from about 0.5% to 5% w / w of the total composition, even more preferably still, from about 0.5% to 3% w / w of the total composition); and

[0118] (v) one or more further pesticides selected from the group consisting of cyproconazole, difenoconazole, hexaconazole, prothioconazole, propiconazole, tebuconazole, mancozeb, chlorothalonil, benzovindiflupyr and pydiflumetofen (preferably, present at a percentage (%) of from 0.01 % to 70% w / w (weight / weight) of the total composition, more preferably of from about 1 % to 50% w / w (weight / weight) of the total composition, even more preferably, from about 3% to 45% w / w of the total composition, even more preferably still, from about 5% to 40% w / w of the total composition).

[0119] Even more preferably, there is provided an aqueous composition comprising,

[0120] (i) methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate (preferably present at a percentage (%) of from 0.01 % to 70% w / w (weight / weight) of the total composition, more preferably of from about 1 % to 60% w / w (weight / weight) of the total composition, even more preferably, from about 3% to 55% w / w of the total composition, even more preferably still, from about 5% to 45% w / w of the total composition);

[0121] (ii) a polyethylene oxide)-poly(propylene oxide)-poly(ethylene oxide) block copolymer having a molecular weight of from 5,000 g / mol to 6,600 g / mol (preferably, present at a percentage (%) of from 0.01 % to 30% w / w, preferably from 0.1 % to 15% by w / w, and more preferably from 0.5% to 5% w / w, over the total weight of the composition);

[0122] (iii) an acrylic graft copolymer comprising a backbone obtained from acrylate and / or methacrylate monomers, and side chains comprising polyethylene glycol and / or mono-ether polyethylene glycol ( preferably, present at a percentage (%) of from 0.0005% to 30% w / w, more preferably from 0.01 % to 20% by w / w, and even more preferably from 0.1 % to 10% w / w, over the total weight of the composition);

[0123] (iv) at least one sulfonate and / or sulfate selected from the group consisting of triethanolamine C10-13- alkyl benzenesulfonic acid and tristyryl phenol sulfate ammomium salt (more preferably, triethanolamine dodecylbenzenesulfonate) (preferably, present at a percentage of from about 0.1 % to 30% w / w (weight / weight) of the total composition, more preferably, from about 0.1 % to 15% w / w of the total composition, more preferably, from about 0.5 % to 10% w / w of the total composition, even more preferably, from about 0.5% to 5% w / w of the total composition, even more preferably still, from about 0.5% to 3% w / w of the total composition); and

[0124] (v) one or more further pesticides (preferably one or two) selected from the group consisting of prothioconazole, mancozeb and pydiflumetofen (preferably, prothioconazole) (preferably, present at a percentage (%) of from 0.01 % to 70% w / w (weight / weight) of the total composition, more preferably of from about 1% to 50% w / w (weight / weight) of the total composition, even more preferably, from about 3% to 45% w / w of the total composition, even more preferably still, from about 5% to 40% w / w of the total composition).

[0125] In another embodiment there is provided a composition (preferably an aqueous composition) comprising:

[0126] (i) methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate; and

[0127] (iii) an acrylic graft copolymer (preferably as further defined herein).

[0128] In another preferred embodiment, there is provided a composition (preferably an aqueous composition) comprising,

[0129] (i) methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate; and

[0130] (iv) at least one sulfonate and / or sulfate (preferably as further defined herein).

[0131] The present invention further relates to methods of controlling or preventing infestation of useful plants or plant propagation material and / or harvested food crops by phytopathogenic fungi comprising applying a composition as described herein, to said plants or plant propagation material and / or harvested food crops, to parts thereof or the locus thereof. Preferably, the invention relates to a method of controlling or preventing infestation of useful plants by phytopathogenic fungi comprising applying a composition as described herein, to said plants, to parts thereof or the locus thereof.

[0132] In another embodiment of the invention there is provided a method of controlling or preventing infestation by phytopathogenic fungi (preferably, Phakopsora pachyrhizi) in a plant (preferably, soybean), wherein said phytopathogenic fungi comprises a F129L mutation in the mitochondrial cytochrome b which confers resistance to Qo inhibitors, said method comprising applying to the plant, to parts thereof or the locus thereof, a fungicidal composition as defined herein.

[0133] Preferably, there is provided a method of controlling or preventing infestation by phytopathogenic fungi (preferably, Phakopsora pachyrhizi) in soybean, wherein said phytopathogenic fungi comprises a F129L mutation in the mitochondrial cytochrome b which confers resistance to Qo inhibitors, said method comprising applying to the plant, to parts thereof or the locus thereof, a fungicidal composition as defined herein.

[0134] The stated mutation F129L is made with reference to the amino acid sequence of the Phakopsora pachyrhizi mitochondrial Cytochrome b, Genbank ID NC_014344.1. The corresponding gene is referred to in Genbank ID 9481042.

[0135] The compositions of the invention may be used for controlling a broad spectrum of plant diseases, such as foliar and / or soil-borne pathogens of ornamental, turf, vegetable, field, cereal, and fruit crops. These pathogens may include:

[0136] Oomycetes, including Phytophthora species such as Phytophthora cactorum, Phytophthora capsici, Phytophthora cinnamomi, Phytophthora citricola, Phytophthora citrophthora, Phytophthora erythrose ptica, Phytophthora fragariae, Phytophthora infestans, Phytophthora nicotianae, Phytophthora porri, and Phytophthora sojae Pythium species such as Pythium aphanidermatum, Pythium arrhenomanes, Pythium graminicola, Pythium irregulare and Pythium ultimum other Peronosporales such as Bremia lactucae, Hyaloperonospora parasitica, Hyaloperonospora brassicae, Sclerophthora macrospora, Sclerospora graminicola; Peronospora species including Peronospora destructor, Peronospora farinosa f. sp. spinaciae and Peronospora viciae f. sp. pisi; 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; Albuginales such as Albugo Candida, Albugo occidentalis, and Albugo tragopogonis; and Saprolegniales such as Aphanomyces species, including Aphanomyces cochliodes.

[0137] Ascomycetes, including Mycosphaerellales such as Actinothyrium graminis, Asperisporium caricae, Cercospora species including Cercospora arachidicola, Cercospora beticola, Cercospora brassicicola, Cercospora canescens, Cercospora cf. flagellaris, Cercospora janseana, Cercospora kikuchii, Cercospora lagenariae, Cercospora sojinae, Cercospora sorghi, Cercospora zeae-maydis; Dothistroma septosporum, Fulvia fulva, Mycosphaerella species including Mycosphaerella pomi and Mycosphaerella linicola; Neopseudocercosporella brassicae, Neopseudocercosporella capsellae, Nothopassalora personata, Nothophaeocrytopus gaeumannii, Passalora bataticola, Passalora koepkei, Pseudocercospora griseola, Pseudocercospora musaei, Pseudocercospora vitis, Pseudocercospora fijiensis, Ramularia species including Ramularia beticola and Ramularia collo-cygni; Ramulariopsis gossypii, Ramulariopsis pseudoglycines, Ramulispora sorghi, Scolecostigmina palmivora, 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, 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, Monilinia species including Monilinia fructicola, Monilinia fructigena and Monilinia laxa; Neofabraea perennans, Neofabraea vagabunda, Oculimacula yallundae, Pezicula spp., Pseudopeziza medicaginis, Pseudopeziza tracheiphila, Pyrenopeziza species including Pyrenopeziza brassicae; Rhabdocline pseudotsugae, Rhynchosporium species including Rhynchosporium secalis; Sclerotinia species including Sclerotinia minor, Sclerotinia borealis and Sclerotinia sclerotiorum; Hypocreales such as Acremonium strictum, Albifimbria verrucaria, Claviceps africana, Claviceps purpurea, Fusarium species including Fusarium avenaceum, Fusarium culmorum, Fusarium fujikuroi, Fusarium graminearum, Fusarium incarnatum, Fusarium langsethiae, Fusarium moniliforme, Fusarium oxysporum, Fusarium oxysporum f.sp. cubense, Fusarium poae, Fusarium proliferatum, Fusarium pseudograminearum, Fusarium subglutinans, Fusarium sulphureum, Fusarium tricinctum and Fusarium verticillioides; Gliocladium spp., Neocosmospora phaseoli, Neocosmospora solani, Neonectria Candida, Paramyrothecium roridum, Sarocladium oryzae, Trichoderma species including Trichoderma harzianum, Trichoderma pseudokoningii and Trichoderma viride; Trichothecium roseum and Ustilaginoidea virens; Magnaporthales such as Gaeumannomyces avenae, Gaeumannomyces graminis, Gaeumannomyces graminis tritici, Gaeumannomyces wongoonoo, Magnaporthiopsis poae, Pyricularia species including Pyricularia grisea and Pyricularia oryzae; Pleosporales, such as Altemaria species including Altemaria allii, Altemaria alternata, Altemaria arachidis, Altemaria brassicae, Alternaria brassicicola, Alternaria citri, Alternaria dauci, Alternaria grandisi, Alternaria helianthicola, Altemaria linariae, Alternaria mali, Alternaria porri, Alternaria solan! and Alternaria tomato; Boeremia coffeae, Ascochyta species including Ascochyta pisi and Ascochyta rabiei; Bipolaris maydis, Bipolaris oryzae, Bipolaris sorokiniana, Cochliobolus spp., Corynespora cassiicola, Curvularia species including Curvularia australiensis, Curvularia cactivora and Curvularia lunata; Didymella species including Didymella pinodella and Didymela pinodes; Xenodidymella applanata, Drechslera species including Drechslera glycines; Epicoccum nigrum, Exserohilum turcicum, Helminthosporium species including Helminthosporium solani; Hendersonia creberrima, Leptosphaerulina crassiasca, Neocamarosporium betae, Ophiosphaerella agrostidis, Ophiosphaerella herpotricha, Ophiosphaerella korrae, Ophiosphaerella narmari, Parastagonospora nodorum, Phaeosphaeria herpotrichoides, Phaerosphaeria maydis, Phoma spp., Plenodomus lindquistii, Plenodomus lingam, Pleospora spp., Pseudopyrenochaeta lycopersici, Pyrenophora species including Pyrenophora poae, Pyrenophora teres and Pyrenophora tritici-repentis; Remotididymella destructiva, Stagonospora tainanensis, Stagonosporopsis cucurbitacearum, Stemphylium species including Stemphylium botryosum, Stemphylium solani and Stemphylium vesicarium; Diaporthales such as Anisogramma anonmala, Apiognomonia errabunda, Cytospora platan!, Diaporthe species including Diaporthe amygdali, Diaporthe helianthin, Diaporthe neoviticola and Diaporthe phaseolorum; Dicarpella spp., Discula destructiva, Gnomoniopsis fructicola, Greeneria uvicola, Juglanconis juglandina, Ophiognomonia clavigignenti-juglandacearum, Stenocarpella maydis and Tubakia dryina; Dothideales such as Aureobasidium species including Aureobasidium pullulans; Discosphaerina fulvida; Erysiphales such as Blumeria graminis, Brasiliomyces malachrae, Erysiphe species including Erysiphe betae, Erysiphe cruciferarum, Erysiphe diffusa, Erysiphe heraclei, Erysiphe necator and Erysiphe pisi; Golovinomyces cichoracearum, Golovinomyces orontii, Leveillula taurica, Oidium arachidisi, Oidium neolycoperisci, Phyllactinia guttata, Podosphaera species including Pososphaera aphanis, Podosphaera fuliginea, Podosphaera fusca, Podosphaera leucotricha, Podosphaera macularis, Podosphaera mors-uvae, Podosphaera pannosa, Podosphaera tridactyla and Podosphaera xanthii; Glomerellales such as Colletotrichum species including Colletotrichum acutatum, Colletotrichum cereale, Colletotrichum chrysanthemi, Colletotrichum cliviicola, Colletotrichum coccodes, Colletotrichum fragariae, Colletotrichum gloeosporioides, Colletotrichum graminicola, Colletotrichum lentis, Colletotrichum lindemuthianum, Colletotrichum musae, Colletotrichum orbiculare, Colletotrichum siamense and Colletotrichum truncatum; Glomerella cingluata, Glomerella gossypii, Musicillium theobromae, Plectosphaerella cucumerina, Verticillium species including Verticillium dahlia; Venturiales such as Venturia species including Venturia carpophila, Venturia effusa, Venturia inaequalis, Venturia oleaginea, and Venturia pyrina; Xylariales such as Eutypa lata, Microdochium albescens, Microdochium majus, Microdochium nivale, Microdochium paspali, Microdochium sorghi, Physalospora abdita, Rosellinia spp. and Seimatosporium mariae; Botryosphaeriales such as Botryosphaeria species including Botryosphaeria dothidea; Diplodia species including Diplodia seriata; Dothiorella aromatica, Lasiodiplodia theobromae, Macrophoma theicola, Macrophomina phaseolina, Phyllosticta ampelicida and Phyllosticta cucurbitacearum; Eurotiales such as Aspergillus species including Aspergillus flavus, Aspergillus fumigatus, Aspergillus niger and Aspergillus terreus; Penicillium species including Penicillium digitatum, Penicillium expansum and Penicillium italicum; Microascales such as Berkeleyomyces basicola, Thielaviopsis paradoxa, Ceratocystis species including Ceratocystis fimbriata, Ceratocystis manginecans and Ceratocystis platan!; Scedosporium species including Scedosporium apiospermum and Scedosporium prolificans; Myriangiales such as Elsinoe species including Elsinoe ampelina and Elsinoe perseae; Ophiostomatales such as Leptographium lundbergii, Leptographium microsporum, Ophiostoma novo-ulmi, Ophiostoma piceae and Sporothrix spp.; Pezizomycetes such as Phymatotrichopsis omnivore and Polyscytalum pustulans; Phyllachorales such as Gibellina cerealis, Phyllachora maydis and Phyllachora pomigena; Amphisphaeriales such as Griphosphaeria corticola, Lepteutypa cupressi and Pestalotia rhododendri; Capnodiales such as Capnodium ramosum and Schizothyrium pomi; Chaetothyriales such as Phialophroa spp.; Cladosporiales such as Cladosporium species including Cladosporium oxysporum, Cladosporium cucumerinum and Cladosporium allii-cepae; Rhytismatales such as Lophodermium seditiosum and Naemacyclus spp.; Saccharomycetales such as Cephaloascus species including Cephaloascus fragrans; Geotrichum candidum, Candida species including Candida glabrata, Candida krusei, Candida lusitaniae, Candida parapsilosis, Candida albicans and Candida tropicalis; Sordariales such as Chaetomium spp. and Monosporascus cannonballus; Sordariomycetes such as Wongia garrettii and Wongia griffinii; Taphrinales such as Taphrina bullata and Taphrina deformans; Onygenales such as Ajellomyces capsulatus, Blastomyces dermatitidis, Coccidioides species including Coccidioides immitis; Epidermophyton spp., Histoplasma spp., Microsporum spp., Trichophyton spp., and Paracoccidioides species including Paracoccioides brasiliensis; and others such as Hymenula cerealis, Petriellidum spp., and Septocyta ruborum.

[0138] Basidiomycetes, including Pucciniales such as Cerotelium fici, Chrysomyxa arctostaphyli, Coleosporium ipomoeae, Cron art! urn ribicola, Gymnosporangium juniperi-virginianae, Gymnosporangium sabinae, Hemileia species including Hemileia vastatrix; Melampsora medusae, Melampsora lini, Phakopsora ampelopsidis, Phakopsora pachyrhizi, Phragmidium mucronatum, Puccinia species including Puccinia aim, Puccinia arachidis, Puccinia asparagi, Puccinia cacabata, Puccinia coronata, Puccinia graminis, Puccinia helianthi, Puccinia hieracii, Puccinia horde!, Puccinia horiana, Puccinia melanocephala, Puccinia polysora, Puccinia porri, Puccinia recondita, Puccinia sorghi, Puccinia striiformis, Puccinia striiformis f.sp. horde!, Puccinia striiformis f.sp. tritici and Puccinia triticina; Pucciniastrum coryli, Tranzschelia discolor, Uromyces species including Uromyces betae, Uromyces pis! and Uromyces viciae-fabae; Tilletiales such as Neovossia moliniae, and Tilletia species including Tilletia caries and Tilletia controversa; Ustilaginales such as Sporisorium reilianum and Ustilago species including Ustilago maydis, Ustilago segetum var. nuda, Ustilago segetum var. tritici and Ustilago striiformis; Urocystidales such as Urocystis species including Urocystis agropyri; Agaricales such as Marasmiellus inoderma, Mycena spp., Moniliophthora roreri and Moniliophthora perniciosa; Cantharellales such as Sclerotium spp. and Typhula species including Typhula incarnata and Typhula ishikariensis; Ceratobasidiales such as Waitea circinata, and Rhizoctonia species including Rhizoctonia cerealis, Rhizoctonia solan! and Rhizoctonia theobromae; Atheliales such as Athelia rolfsii; Corticiales such as Corticium invisum and Laetisaria fuciformis; Cystodilobasidiales such as Itersonilia perplexans; Entylomatales such as Entyloma calendulae f.sp. dahliae and Entylomella microspore; Exobasidiales such as Exobasidium vexans; Hymenochaetales such as Phellinus igniarius; Russulales such as Stereum hirsutum; and Tremellales such as Cryptococcus species including Cryptococcus neoformans. Zygomycetes, including Mucorales such as Choanephora cucurbitarum, Mucor spp., Rhizopus oryzae, Absidia corymbifera and Rhizomucor pusillus.

[0139] Blastocladiomycetes, including Physoderma maydis. as well as diseases caused by other species and genera closely related to those listed above.

[0140] In addition to their fungicidal activity, the compositions may also have activity against diseases caused by Actinobacteria such as Streptomyces scabiei; Proteobacteria such as 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; Cercozoa such as Polymyxa betae, Polymyxa graminis and Spongospora subterranea; and Bigyra such as Labyrinthula zosterae. as well as diseases caused by other species and genera closely related to those listed above.

[0141] The compositions as disclosed herein are particularly effective against phytopathogenic fungi belonging to the following classes: Ascomycetes (e.g, Venturia, Podosphaera, Erysiphe, Monilinia, Mycosphaerella, Uncinula); Basidiomycetes (e.g, the genus Hemileia, Rhizoctonia, Phakopsora, Puccinia, Ustilago, Tilletia); Fungi imperfecti (also known as Deuteromycetes; e.g. Botrytis, Helminthosporium, Rhynchosporium, Fusarium, Septoria, Cercospora, Alternaria, Pyricularia and Pseudocercosporella); Oomycetes (e.g, Phytophthora, Peronospora, Pseudoperonospora, Albugo, Bremia, Pythium, Pseudosclerospora and Plasmopara).

[0142] Crops are to be understood as being those which are naturally occurring, obtained by conventional methods of breeding, or obtained by genetic engineering. They include crops which contain so-called output traits (e.g. improved storage stability, higher nutritional value and improved flavour).

[0143] Crops are to be understood as also including those crops which have been rendered tolerant to herbicides like bromoxynil or classes of herbicides such as ALS-, EPSPS-, GS-, HPPD- and PPO- inhibitors. An example of a crop that has been rendered tolerant to imidazolinones, e.g. imazamox, by conventional methods of breeding is Clearfield® summer canola. Examples of crops that have been rendered tolerant to herbicides by genetic engineering methods include e.g. glyphosate- and glufosinate-resistant maize varieties commercially available under the trade names RoundupReady®, Herculex I® and LibertyLink®.

[0144] Crops are also to be understood as being those which naturally are or have been rendered resistant to harmful insects. This includes plants transformed by the use of recombinant DNA techniques, for example, to be capable of synthesising one or more selectively acting toxins, such as are known, for example, from toxin-producing bacteria. Examples of toxins which can be expressed include 8-endotoxins, vegetative insecticidal proteins (Vip), insecticidal proteins of bacteria colonising nematodes, and toxins produced by scorpions, arachnids, wasps and fungi.

[0145] An example of a crop that has been modified to express the Bacillus thuringiensis toxin is the Bt maize KnockOut® (Syngenta Seeds). An example of a crop comprising more than one gene that codes for insecticidal resistance and thus expresses more than one toxin is VipCot® (Syngenta Seeds). Crops or seed material thereof can also be resistant to multiple types of pests (so-called stacked transgenic events when created by genetic modification). For example, a plant can have the ability to express an insecticidal protein while at the same time being herbicide tolerant, for example Herculex I ® (Dow AgroSciences, Pioneer Hi-Bred International).

[0146] The fungicidal compositions as disclosed herein, may be used in controlling or preventing phytopathogenic diseases, especially phytopathogenic fungi (such as Phakopsora pachyrhizi) on transgenic soybean plants.

[0147] In particular, transgenic soybean plants expressing toxins, for example insecticidal proteins such as delta-endotoxins, e.g. CrylAc (CrylAc Bt protein). Accordingly, this may include transgenic soybean plants comprising event MON87701 (disclosed in W02009 / 064652, as well as WO2014 / 170327 (eg, see paragraph

[0008] reference to Intacta RR2 PRO® soybean)), event MON87751 (disclosed in WO2014 / 201235) or event DAS-81419-2 (aka Conkesta™ Soybean, described in WO2013016527).

[0148] Useful transgenic events in transgenic soybean plants, which can be treated according to the invention, include event DAS-44406-6 / pDAB8264.44.06.1 (soybean, herbicide-tolerance, disclosed in WO2012 / 075426); event DAS-81419-2 (aka Conkesta™ Soybean, described in WO2013016527 (aka Conkesta™ Enlist E3™ Soybean, DAS-81419-2 x DAS-44406-6); event DAS-14536- 7 / pDAB8291 .45.36.2 (soybean, herbicide-tolerance, disclosed in WO2012 / 075429); DAS-68416-4 (soybean, herbicide-tolerance, ATCC Accession No. PTA-10442, disclosed in WO201 1 / 066384, WO201 1 / 066360); event DP-305423-1 (soybean, quality mark, disclosed in W02008 / 054747); event DP-356043-5 (soybean, herbicide-tolerance, deposited as ATCC PTA-8287, disclosed in W02008 / 002872); event FG72 (soybean, herbicide-tolerance, disclosed in WO2011 / 063413); event LL27 (soybean, herbicide-tolerance, disclosed in W02006 / 108674); event LL55 (soybean, herbicidetolerance, disclosed in WO 2006 / 108675); event EE-GM3 / FG72 (soybean, herbicide-tolerance) optionally stacked with event EE-GM1 / LL27 or event EE-GM2 / LL55 (disclosed in WO201 1 / 063413); event MON87701 (soybean, insect control, disclosed in W02009 / 064652, WO2014 / 170327); event MON87705 (soybean, improved fatty acid profile, herbicide-tolerance, disclosed in WO2010 / 037016); event MON87751 (lepidopteran-resistant, ATCC accession no. PTA-120166. disclosed in WO2014 / 201235); event MON87708 (soybean, herbicide-tolerance, disclosed in WO2011 / 034704); event MON87712 (soybean, yield, disclosed in WO2012 / 051 199); event MON87754 (soybean, quality feature, disclosed in WO2010 / 024976); event MON87769 (soybean, quality attribute, disclosed in W02009 / 102873); event MON89788 (soybean, herbicide-tolerance, disclosed in W02006 / 130436); event SYHT0H2 / SYN-000H2-5 (soybean, herbicide-tolerance, disclosed in WO2012 / 082548); event DAS-21606-3 (soybean, herbicide-tolerance, disclosed in WO2012 / 033794); event 8264.44.06.1 (soybean, stacked herbicide-tolerance, disclosed in W02022 / 012075426); event pDAB8291 .45.36.2 (soybean, stacked herbicide-tolerance, disclosed in WO2012 / 075429); event pDAB8264.42.32.1 (soybean, stacked herbicide-tolerance, disclosed in WO2013 / 010094); event A2704-12 (glufosinate tolerance, disclosed in W02006 / 108647); event A5547-127 (phosphinothricin tolerant, disclosed in W02006 / 108675); event BPS-CV127- 91 (herbicide tolerance, disclosed in WO 2010 / 080829); event GU262 (phosphinothricin tolerant, described in APHIS regulatory reference US 98-238-01 p).

[0149] Particularly useful transgenic events in transgenic soybean plants, which can preferably be treated according to the invention, include event A2704-12 (glufosinate tolerance, disclosed in W02006 / 108647), event A5547-127 (phosphinothricin tolerant, disclosed in W02006 / 108675); event GU262 (phosphinothricin tolerant, described in APHIS regulatory reference US 98-238-01 p); event MON89788 (disclosed in W02006 / 130494A; event DP-305423-1 (soybean, quality mark, disclosed in W02008 / 054747); event MON87701 (soybean, insect resistant, disclosed in W02009 / 064652); event MON87705 (soybean, improved fatty acid profile, herbicide-tolerance, disclosed in WO2010 / 037016 or US20100080887A); event MON87769 (soybean, quality attribute, disclosed in W02009 / 102873 or US20110067141A); event FG72 (soybean, herbicide-tolerance, disclosed in WO201 1 / 063413); event MON87712 (soybean, yield, disclosed in WO2012 / 051199); event BPS- CV127-9 (soybean, herbicide tolerance, deposited as NCIMB No. 41603, disclosed in WO2010 / 08082); event DAS-68416-4 (soybean, herbicide-tolerance, ATCC Accession No. PTA-10442, disclosed in WO201 1 / 066384, WO2011 / 066360); event SYHT0H2 / SYN-000H2-5 (soybean, herbicide-tolerance, disclosed in WO2012 / 082548); event DAS-44406-6 / pDAB8264.44.06.1 (soybean, herbicide-tolerance, disclosed in WO2012 / 075426); event MON87751 (lepidopteran-resistant, ATCC accession no. PTA- 120166. disclosed in WO2014 / 201235); event MON87708 (soybean, herbicide-tolerance, disclosed in WO2011 / 034704) and event GMB151 (also called BCS-GM151-6, HPPD tolerance, disclosed in WO2018119364A1).

[0150] Furthermore, such a list of transgenic events is provided by the United States Department of Agriculture's (USDA) Animal and Plant Health Inspection Service (APHIS) and can be found on their website on the World Wide Web at aphis.usda.gov.

[0151] The term “event” as used herein refers to the event name that relates to a unique DNA recombination event that took place in one plant cell and which was then used to generate an entire transgenic plant. Detailed information on the events and associated products can be found on http: / / www.isaaa.org / gmapprovaldatabase. The events listed herein have been introduced into plants that are now commercially available.

[0152] Commercially available examples of transgenic soybeans, which can preferably be treated by the compositions according to the invention, include commercially available products such as plant seeds, which are under the ROUNDUP READY 2 XTEN®, INTACTA RR2 PRO®, VISTIVE® GOLD, Conkesta E3®, Conkesta Enlist E3™, LibertyLink® and / or XtendFlex® trade names are sold or distributed.

[0153] In another embodiment of the invention there is provided a method of controlling or preventing infestation by phytopathogenic fungi (preferably, Phakopsora pachyrhizi) in a soybean variety, said method comprising applying to the soybean variety selected from the list consisting of TMG 7062, TMG 7161 , TMG 7261 , to TMG7368 IPRO (disclosed in W02009079729), TMG7062 IPRO, TMG 7063 IPRO, TMG 7061 IPRO, BRS51 1 soybean, BRS 531 soybean and Soy-BRS 539, to parts thereof or the locus thereof, a fungicidal composition as defined herein.

[0154] As used herein, the term “Bt soybean plant” refers to soybean plants that are genetically engineered soybeans that produce an insecticidal protein like the one naturally produced by the bacteria species Bacillus thuringiensis, for example by the genes CrylA(a), CrylA(b), CrylA(c), CryllA, CrylllA, CrylllB2, Cry9c, Cry2Ab, Cry3Bb and CrylF and also combinations thereof. These soybeans that are genetically engineered to produce the same toxin as Bacillus thuringiensis (Bt) in every cell of the plant, with the goal of protecting the soybean from pests, are referred to herein as "Bt soybeans”. Examples Bt soybean plants are Intacta RR2 PRO®, or Conkesta Enlist E3®. In a preferred embodiment of the invention there is provided a method of controlling or preventing infestation by phytopathogenic fungi (preferably, Phakopsora pachyrhizi) in a transgenic soybean plant, said method comprising applying to the plant, to parts thereof or the locus thereof, a fungicidal composition as defined herein.

[0155] The term “locus” as used herein means fields in or on which plants are growing, or where seeds of cultivated plants are sown, or where seed will be placed into the soil. It includes soil, seeds, and seedlings, as well as established vegetation.

[0156] The term “plants” refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, foliage, and fruits.

[0157] The term “plant propagation material” is understood to denote generative parts of the plant, such as seeds, which can be used for the multiplication of the latter, and vegetative material, such as cuttings or tubers, for example potatoes. There can be mentioned for example seeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes and parts of plants. Germinated plants and young plants which are to be transplanted after germination or after emergence from the soil, may also be mentioned. These young plants can be protected before transplantation by a total or partial treatment by immersion. Preferably “plant propagation material” is understood to denote seeds.

[0158] The compositions according to the invention can be applied to the crop area or plant to be treated, simultaneously or in succession with further compounds. These further compounds can be e.g. fertilizers or micronutrient donors or other preparations, which influence the growth of plants. They can also be selective herbicides or non-selective herbicides as well as insecticides, fungicides, bactericides, nematicides, molluscicides or mixtures of several of these preparations, if desired together with further carriers, surfactants or application promoting adjuvants customarily employed in the art of formulation.

[0159] The rate at which the compositions of the invention are applied will depend upon the particular type of phytopathogen, etc, to be controlled, the degree of control required and the timing and method of application which can be readily determined by the person skilled in the art. In general, the compositions of the invention can be applied at an application rate of between 0.005 kilograms / hectare (kg / ha) and about 5.0 kg / ha, based on the total amount of active ingredient in the composition. An application rate of between about 0.1 kg / ha and about 1 .5 kg / ha is preferred, with an application rate of between about 0.1 kg / ha and 0.5 kg / ha being especially preferred.

[0160] In an aqueous composition comprising the fungicidal composition according to the invention (eg, a tank-mix composition), the one or more additional fungicidal active ingredients may be added separately prior to crop application.

[0161] EXAMPLES

[0162] The Examples which follow serve to illustrate the invention.

[0163] Table A - Surfactant description

[0164]

[0165] Table B - Additional components in examples

[0166] Preparation Examples

[0167] Example 1 - General Preparation Method of Aqueous Formulations This example provides compositions which are a millbase (comprising methyl (Z)-2-(5-cyclohexyl-2- methyl-phenoxy)-3-methoxy-prop-2-enoate) and which may be used to prepare further compositions or formulations. The skilled person would appreciate that these millbase examples can include additional well-known formulation components as necessary. The compositions shown in Table 1a and 1 b below were prepared by charging water, the dispersing agent and mixing all components until a solution is obtained. After that, the antifoam (Xiameter ACPI 500) was added to the solution and the obtained mixture mixed. The active ingredient or ingredients (for example, methyl (Z)-2-(5-cyclohexyl-2-methyl- phenoxy)-3-methoxy-prop-2-enoate) are then charged, and mixed until a homogeneous sample is obtained. The obtained suspension was milled on a Shaker mill (Fristch mill) using 1 mm glass beads. Milling time used is similar for all samples. Milling time: 2 x 30 min and temperature is kept below 35°C. After milling, the sample aspects are reported and milling guality is assessed by optical microscopy.

[0168] Table 1a - Millbase compositions comprising methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy- prop-2-enoate (as the active ingredient) * Visual inspection demonstrated that agglomerates were visible on the wall of the glass vessel, not necessarily observed under optical microscopy.

[0169] Table 1 b - Millbase compositions comprising methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy- prop-2-enoate and prothioconazole (as active ingredients)

[0170] Example 2 - Preparation of Suspension Concentrates

[0171] The above-mentioned compositions (for example F5) can be further used as a technical concentre / millbase to prepare a suspension concentrate (SC) formulation according to the present invention. Into a vessel eguipped with a paddle stirrer, charge the millbase composition (for example F5), and add under agitation additional dispersant(s), wetting agent(s), biocide(s), antifreeze, rheology modifier(s) and finally water to adjust the active ingredient content to the desired strength. The biocide(s), the anti-freeze, the viscosity modifier(s) added to form the suspension concentrate are well- known formulation additives. If required, additional formulation additives could be used, such as a pH modifier.

[0172] To prepare a Suspension Concentrate with 37.209%w / w active ingredient (methyl (Z)-2-(5-cyclohexyl- 2-methyl-phenoxy)-3-methoxy-prop-2-enoate), the skilled person would appreciate that using, for example, 74.4 %w / w of F5 would be necessary.

[0173] To prepare a Suspension Concentrate with 9.686%w / w active ingredient (methyl (Z)-2-(5-cyclohexyl-2- methyl-phenoxy)-3-methoxy-prop-2-enoate), the skilled person would appreciate that using, for example, 19.4 %w / w of F5 would be necessary.

[0174] Table 2 below shows examples of suspension conentrates according to the invention.

[0175] Table 2 - Suspension concenterate example

[0176] * component derived from the technical concentre / millbase

[0177] ♦ component added to the technical concentre / millbase

[0178] Brief Description of the Drawings

[0179] The morphology & size of the active compound suspension was examined by optical microscopy after completion of the milling operations. The obtained dispersions were applied on microscope slides (2.5 x 7.5 cm) and covered with cover glass. The microscopy pictures disclosed were taken using a x20 magnification objective using a microscope equipped with polarized filters.

[0180] Figure 1 - F1 Optical microscopy image after milling. Figure 2 - F2 Optical microscopy image after milling.

[0181] Figure 3 - F3 Optical microscopy image after milling.

[0182] Figure 4 - F4 Optical microscopy image after milling.

[0183] Figure 5 - F5 Optical microscopy image after milling.

[0184] Figure 6 - F6 Optical microscopy image after milling.

[0185] Figure 7 - F7 Optical microscopy image after milling.

[0186] These images combined with visual observations demonstrate that the combination of methyl (Z)-2-(5- cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate and a polyoxyalkylene copolymer give formulations with superior properties, particualry with regard to homogeneity.

Claims

CLAIMS:1 . A composition comprising,(i) methyl (Z)-2-(5-cyclohexyl-2-methyl-phenoxy)-3-methoxy-prop-2-enoate; and(ii) a polyoxyalkylene copolymer.

2. The composition according to claim 1 , wherein the composition is an aqueous composition.

3. The composition according to claim 1 or claim 2, wherein the polyoxyalkylene copolymer is a polyethylene oxide)-poly(propylene oxide)-poly(ethylene oxide) block copolymer.

4. The composition according to any one of claims 1 to 3, wherein the polyoxyalkylene copolymer has a molecular weight of from 1 ,000 to 15,000 g / mol.

5. The composition according to any one of claims 1 to 4, wherein the polyoxyalkylene copolymer has a molecular weight of from 4,000 to 7,000 g / mol.

6. The composition according to any one of claims 1 to 5, wherein the polyoxyalkylene copolymer is present at a percentage of from about 0.5% to 10% w / w (weight / weight) of the total composition.

7. The composition according to any one of claims 1 to 6, further comprising (iii) an acrylic graft copolymer.

8. The composition according to claim 7, wherein the acrylic graft copolymer comprises a backbone obtained from acrylate and / or methacrylate monomers, and side chains comprising polyethylene glycol and / or mono-ether polyethylene glycol.

9. The composition according to any one of claims 1 to 8, further comprising (iv) at least one sulfonate and / or sulfate.

10. The composition according to claim 9, wherein the sulfonate and / or sulfate is an amine salt.

11. The composition according to claim 9 or claim 10, wherein the sulfonate and / or sulfate is selected from the group consisting of triethanolamine C10-13-alkyl benzenesulfonic acid and tristyryl phenol sulfate ammomium salt.

12. The composition according to any one of claims 1 to 11 , further comprising one or more formulation additives selected from the group consisting of an anti-freeze agent, an anti-foamagent, an anti-bacterial agent (or biocide), a viscosity modifier, a pH modifier, and any mixture thereof.

13. The composition according to any one of claims 1 to 12, further comprising (v) one or more further pesticides selected from the group consisting of bixafen, fenpyrazamine, copper sulfate, copper hydroxide, triclopyricarb, acibenzolar, acibenzolar-S-methyl, copper oxychloride, copper oxide, azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, furametpyr, hexaconazole, imazalil, imibenconazole, ipconazole, metconazole, myclobutanil, pefurazoate, penconazole, prothioconazole, pyrifenox, prochloraz, propiconazole, pyrisoxazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triflumizole, triticonazole, fenarimol, nuarimol, dodemorph, fenpropidin, fenpropimorph, spiroxamine, tridemorph, boscalid, carboxin, fenfuram, flutolanil, mepronil, oxycarboxin, penthiopyrad, thifluzamide, azoxystrobin, bifemetstrobin, dimoxystrobin, fenaminstrobin, flufenoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, trifloxystrobin, orysastrobin, picoxystrobin, pyraclostrobin, pyrametostrobin, pyraoxystrobin, mancozeb, chlorothalonil, cyclobutrifluram, famoxadone, fenamidone, fluazinam, fluoxytioconazole, fluxapyroxad, fenhexamid, pyribencarb, triforine, isopyrazam, sedaxane, benzovindiflupyr, pydiflumetofen, isoflucypram, fluindapyr, mandestrobin, pyraziflumid, inpyrfluxam, mefentrifluconazole, ipfentrifluconazole, penflufen, florylpicoxamid, metarylpicoxamid, isofetamid, ethyl 1-[[4-[[2-(trifluoromethyl)-1 ,3-dioxolan-2- yl]methoxy]phenyl]methyl]pyrazole-3-carboxylate, ethyl 1-[[4-[(Z)-2-ethoxy-3,3,3-trifluoro-prop- 1 -enoxy]phenyl]methyl]pyrazole-3-carboxylate, methyl N-[[4-[1 -(4-cyclopropyl-2,6-difluoro- phenyl)pyrazol-4-yl]-2-methyl-phenyl]methyl]carbamate, methyl N-[[4-[1 -(2,6-difluoro-4- isopropyl-phenyl)pyrazol-4-yl]-2-methyl-phenyl]methyl]carbamate, fluopyram, flufenoxadiazam, metyltetraprole, enoxastrobin, coumoxystrobin, (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, (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, 2-tert-butyl-4-(3-chloro-2-fluoro-phenoxy)-N-[2-(2,4- dimethylphenyl)-2,2-difluoro-ethyl]pyrazole-3-carboxamide, methyl (2R)-2-[2-chloro-4-(4- chlorophenoxy)phenyl]-2-hydroxy-3-(1 ,2,4-triazol-1-yl)propanoate, methyl 2-[2-chloro-4-(4- chlorophenoxy)phenyl]-2-hydroxy-3-(1 , 2 ,4-tri azo I- 1 -yl)propanoate, N'-[5-bromo-2-methyl-6- [(1 S)-1 -methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5-bromo-2- methyl-6-[(1 R)-1-methyl-2-propoxy-ethoxy]-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5- bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5- chloro-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N'-[5- bromo-2-methyl-6-(1-methyl-2-propoxy-ethoxy)-3-pyridyl]-N-isopropyl-N-methyl-formamidine, N'-[5-bromo-2-methyl-6-(2-propoxypropoxy)-3-pyridyl]-N-ethyl-N-methyl-formamidine, N- isopropyl-N’-[5-methoxy-2-methyl-4-(2, 2, 2-trifluoro-1 -hydroxy-1 -phenyl-ethyl)phenyl]-N-methyl- formamidine, N’-[4-(1-cyclopropyl-2,2,2-trifluoro-1-hydroxy-ethyl)-5-methoxy-2-methyl-phenyl]- N-isopropyl-N-methyl-formamidine, N-ethyl-N’-[5-methoxy-2-methyl-4-[(2- trifluoromethyl)oxetan-2-yl]phenyl]-N-methyl-formamidine, N-ethyl-N’-[5-methoxy-2-methyl-4-[(2-trifuoromethyl)tetrahydrofuran-2-yl]phenyl]-N-methyl-formamidine, N-[(1 R)-1-benzyl-3- chloro-1 -methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide, N-[(1 S)-1 -benzyl-3-chloro-1 - methyl-but-3-enyl]-8-fluoro-quinoline-3-carboxamide, N-[(1 R)-1 -benzyl-3,3,3-trifluoro-1 -methyl- propyl]-8-fluoro-quinoline-3-carboxamide, N-[(1 S)-1-benzyl-3,3,3-trifluoro-1-methyl-propyl]-8- fluoro-quinoline-3-carboxamide, N-[(1 R)-1-benzyl-1 ,3-dimethyl-butyl]-7,8-difluoro-quinoline-3- carboxamide, N-[(1 S)-1-benzyl-1 ,3-dimethyl-butyl]-7,8-difluoro-quinoline-3-carboxamide, 8- fluoro-N-[(1 R)-1 -[(3-fluorophenyl)methyl]-1 ,3-dimethyl-butyl]quinoline-3-carboxamide, 8-fluoro- N-[(1 S)-1 -[(3-fluorophenyl)methyl]-1 ,3-dimethyl-butyl]quinoline-3-carboxamide, N-[(1 R)-1 - benzyl-1 ,3-dimethyl-butyl]-8-fluoro-quinoline-3-carboxamide, N-[(1 S)-1 -benzyl- 1 ,3-dimethyl- butyl]-8-fluoro-quinoline-3-carboxamide, N-((1 R)-1 -benzyl-3-chloro-1 -methyl-but-3-enyl)-8- fluoro-quinoline-3-carboxamide, N-((1 S)-1-benzyl-3-chloro-1-methyl-but-3-enyl)-8-fluoro- quinoline-3-carboxamide, 1 -(6,7-dimethylpyrazolo[1 , 5-a] py rid in-3-y l)-4 , 4 , 5-trifl u o ro-3 , 3- dimethyl-isoquinoline, 1-(6,7-dimethylpyrazolo[1 ,5-a]pyridin-3-yl)-4,4,6-trifluoro-3,3-dimethyl- isoquinoline, 4,4-difluoro-3,3-dimethyl-1 -(6-methylpyrazolo[1 ,5-a]pyridin-3-yl)isoquinoline, 4,4- difluoro-3,3-dimethyl-1 -(7-methylpyrazolo[1 ,5-a]pyridin-3-yl)isoquinoline, 1 -(6-chloro-7-methyl- pyrazolo[1 ,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline, 1 -(4,5- dimethylbenzimidazol-1 -yl)-4,4,5-trifluoro-3,3-dimethyl-isoquinoline, 1 -(4,5- dimethylbenzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-isoquinoline, 6-chloro-4,4-difluoro-3,3- dimethyl-1-(4-methylbenzimidazol-1-yl)isoquinoline, 4,4-difluoro-1-(5-fluoro-4-methyl- benzimidazol-1-yl)-3,3-dimethyl-isoquinoline, 3-(4,4-difluoro-3,3-dimethyl-1-isoquinolyl)-7,8- dihydro-6H-cyclopenta[e]benzimidazole, 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]- 1 -(1 , 2 ,4-tri azo I- 1 -yl)propan-2-ol, 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1 -(1 ,2,4- triazol-1 -yl)propan-2-ol, 3-[2-(1 -chlorocyclopropyl)-3-(2-fluorophenyl)-2-hydroxy- propyl]imidazole-4-carbonitrile, 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2- hydroxy-propyl]imidazole-4-carbonitrile, (5-methyl-2-pyridyl)-[4-[5-(trifluoromethyl)-1 ,2,4- oxadiazol-3-yl]phenyl]methanone, (3-methylisoxazol-5-yl)-[4-[5-(trifluoromethyl)-1 ,2,4- oxadiazol-3-yl]phenyl]methanone, 2-oxo-N-propyl-2-[4-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3- yl]phenyl]acetamide, ethyl 1-[[5-[5-(trifluoromethyl)-1 ,2,4-oxadiazol-3-yl]-2- thienyl]methyl]pyrazole-4-carboxylate, 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-carbonimidoyl]-4-[5-(trifluoromethyl)-1 ,2,4- oxadiazol-3-yl]benzamide.

14. The composition according to any one of claims 1 to 13, wherein the composition is a suspension concentrate.

15. A method of controlling or preventing infestation of useful plants by phytopathogenic fungi comprising applying a composition according to one of claims 1 to 14, to said plants, to parts thereof or the locus thereof.

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