An herbicidal formulation comprising pyroxasulfone and metribuzin

Abstract

The present invention provides an aqueous pyroxasulfone-metribuzin-based suspension concentrate (SC) composition comprising a particular wetting agent(s). The compositions of the invention are useful in controlling weed.

Description

AN HERBICIDAL FORMULATION COMPRISING PYROXASULFONE ANDME TRIBUZINTECHNICAL FIELD

[0001] The present invention provides a suspension concentrate (SC) composition comprising pyroxasulfone and metribuzin in the form of suspended particles; at least one particular wetting agent; and water. The compositions of the invention are useful in controlling weed.BACKGROUND ART

[0002] Suspension concentrates (SCs) are formulations, wherein the active ingredient(s) is present in the form of finely divided solid particles, which are suspended (dispersed) in a liquid dispersing medium such as water or polyhydric alcohols, wherein the active ingredient(s) is insoluble or only sparingly soluble.

[0003] There are several problems known to the skilled person which are sometimes encountered with SCs due to settling during prolonged storage or storage at elevated temperatures, the resistance of settled particles to re-suspension, and the formation of crystalline material upon storage. Consequently, these formulations may be difficult to handle, and the bio-efficacy may be inconsistent.

[0004] Specifically, crystal growth can be a significant issue in SC formulations. It causes an increase in the fundamental particle size of the dispersed active ingredient(s) and can lead to increased formulation viscosity, increased sedimentation affecting homogeneity and suspensibility, blockage of nozzles in the spray tank, as well as reduction in application efficiency and biological efficacy. Crystal growth is most likely to occur when the active ingredient(s) has partial water solubility and can occur through several different mechanisms.

[0005] Pyroxasulfone (3-{ [5-(difluoromethoxy)- 1 -methyl-3-(trifluoromethyl)- 1 / 7-pyrazol- 4-yl]methanesulfonyl]-5,5-dimethyl-4,5-dihydro-l,2-oxazole dimethylisoxazole) is a pyrazole herbicide having a relatively low log P value and solubility in water. Pyroxasulfone has been classified in the Herbicide Resistance Action Committee Group K3 and inhibits the biosynthesis of very-long-chain fatty acids in plants. Specifically, it has been shown that injury symptoms of pyroxasulfone-treated weeds were very similar to those of the very-long- chain fatty acid elongase (VLCFAE)-inhibiting herbicides. Furthermore, pyroxasulfoneinhibited six successive elongase reactions of very-long-chain fatty acids and also reduced unsaturated very-long-chain fatty acids (Nakatani et al., 2016).

[0006] According to the literature, pyroxasulfone can control a large number of annual weeds, particularly grasses, as well as herbicide-resistant weeds. Pyroxasulfone also has high pre-emergence activity and longer residual activity than similar products; and it showed good selectivity for, inter alia, corn, soybeans, wheat, turf, cotton, potato, and onion (Nakatani et al., 2016).

[0007] Metribuzin (3-amino-5-tert-butyl-2-(methylsulfanyl)-l,2,4-triazin-5(4 / / )-one) is a triazinone herbicide and is an inhibitor of photosynthesis in plants. Metribuzin can be absorbed by roots and leaves of the plants and then translocate in the xylem; and is active in the control of grasses and broad-leaved weeds.

[0008] It is highly desirable to prepare highly concentrated (highly loaded) formulations and combine two or more active ingredients in a single formulation. Applying a combination of active ingredients with different modes of action can also provide greater weed control. Yet, preparing metribuzin-based formulations can be challenging since metribuzin can crystallize easily, in particular when mixed with other herbicide partners.

[0009] Therefore, there is a need to develop stable formulations comprising at least two active ingredients such as SC formulations comprising pyroxasulfone and metribuzin.SUMMARY OF INVENTION

[0010] It has now been found, in accordance with the present invention, that particular wetting agents were able, on one hand, to wet both pyroxasulfone and metribuzin, and on the other hand, did not cause crystal growth of metribuzin. This finding is highly important, as it enables to prepare stable SC formulation comprising two active ingredients, more specifically, pyroxasulfone and metribuzin, wherein there is no significant crystal growth of metribuzin and / or pyroxasulfone particles during the preparation of the formulation, as well as after storage at high temperatures for long time (e.g., at 54°C for two weeks).

[0011] In one aspect, the present invention thus provides a suspension concentrate (SC) composition comprising: (i) pyroxasulfone and metribuzin in the form of suspended particles; (ii) a wetting agent selected from the group consisting of: (a) a dialkyl sulfosuccinate salt-based surfactant, (b) an alkoxylate alcohol-based surfactant selected from a (Cio-Cis)-fatty alcohol ethoxylate -based surfactant, a (Ci-Cs)-alkyl alcohol ethylene oxidepropylene oxide copolymer-based nonionic surfactant, and a mixture thereof, (c) a (Cs-Cis)-alkyl sulfate salt-based surfactant, (d) a (Cs-C2o)-alkyl benzene sulfonate salt-based surfactant, (e) a taurate salt-based surfactant, (f) an alkyl naphthalene sulfonate salt-based surfactant, and (g) a combination thereof; and (iii) water.

[0012] In another aspect, the present invention relates to a method of controlling weed comprising applying to a locus, such as a field of crop, an effective amount of a composition as defined herein.DETAILED DESCRIPTION

[0013] In one aspect, disclosed herein is a suspension concentrate (SC) composition comprising:(i) pyroxasulfone and metribuzin in the form of suspended particles;(ii) a wetting agent selected from the group consisting of: (a) a dialkyl sulfosuccinate salt-based surfactant, (b) an alkoxylate alcohol-based surfactant selected from a (Cio-Cis)-fatty alcohol ethoxylate -based surfactant, a (Ci-Cs)-alkyl alcohol ethylene oxide-propylene oxide copolymer-based nonionic surfactant, and a mixture thereof, (c) a (Cs-Ci8)-alkyl sulfate salt-based surfactant, (d) a (Cs-C2o)-alkyl benzene sulfonate salt-based surfactant, (e) a taurate salt-based surfactant, (f) an alkyl naphthalene sulfonate salt-based surfactant, and (g) a combination thereof; and(iii) water.

[0014] The term “alkyl” typically means a linear or branched hydrocarbyl having, e.g., 1-20 carbon atoms which may be interrupted with a heteroatom selected from N, O, and S; and includes, e.g., methyl, ethyl, n-propyl, isopropyl, n-butyl, n-butoxy butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 2,2-dimethylpropyl, n-hexyl, n-octyl, dodecyl, and the like.

[0015] The terms “wetting agent” or “wetter” are used herein interchangeably and refer to a surfactant, i.e., any agriculturally acceptable material which decrease s / lowers the surface tension of water, thereby allowing it to spread and penetrate by, e.g., weakening water’s cohesive properties and strengthening its adhesive properties. The wetting agents comprised within the composition of the invention do not cause / promote / accelerate significant crystal growth of metribuzin.

[0016] Due to the hydrophobic nature of pyroxasulfone, the presence of a wetting agent, is required in order for pyroxasulfone to enter the water phase. Yet, the addition of such surfactants may increase crystal growth of the active ingredient(s) (e.g., particle size higher than about 25 pm), and this can be very problematic for herbicidal formulations. Accordingto the invention, the wetting agents comprised within the SC compositions disclosed herein do not cause significant crystal growth of the particles comprised within the composition during the preparation of said compositions, thereby allowing to obtain highly stable pyroxasulfone-metribuzin-based SC compositions without significant crystal growth of the particles comprised within said compositions (e.g., D90 value of particles lower than 25 pm, preferably lower than 20 pm, more preferably lower than 18 pm, 17 pm, or 15 pm) even after storage for long time (e.g., for at least 5 days, preferably at least a week, more preferably at least 10 days or 14 days) and / or under elevated temperatures (e.g., above room temperature, such as at 54°C).

[0017] Particular dialkyl sulfosuccinate salt-based surfactants referred to herein are di-(C?- Ci2)alkyl sulfosuccinate alkali metal salt-based surfactants or di-(C7-Ci2)alkyl sulfosuccinate alkaline earth metal salt-based surfactants. Non-limiting examples of di-(C?- Ci2)alkyl sulfo succinate alkali metal salt-based surfactants include sodium dioctyl sulfosuccinate (e.g., Aerosol® OT-75 PG and Aerosol® OT-100).

[0018] The term “alkali metal” as used herein refers to the chemical elements lithium (Li), sodium (Na), potassium (K), rubidium (Rb), cesium (Cs), and francium (Fr). Together with hydrogen they constitute group 1, which lies in the s-block of the periodic table and they readily lose their outermost electron to form cations with charge +1.

[0019] The term “alkaline earth metal” as used herein refers to six chemical elements in group 2 of the periodic table, i.e., beryllium (Be), magnesium (Mg), calcium (Ca), strontium (Sr), barium (Ba), and radium (Ra). The alkaline earth metals readily lose two electrons to form cations with charge +2, and an oxidation state of +2.

[0020] Particular (Cio-Cis)-fatty alcohol ethoxylate-based surfactants referred to herein are (Ci2-Ci5)-alcohol ethoxylates. Non-limiting examples of (Ci2-Ci5)-alcohol ethoxylates include BIO-SOFT® N25-12 and an iso-tridecyl alcohol ethoxylate (e.g., Genapol® X-080).

[0021] Particular (Ci-C8)-alkyl alcohol ethylene oxide -propylene oxide copolymer-based nonionic surfactants referred to herein are n-butyl alcohol ethylene oxide-propylene oxide block copolymers, n-butoxy butyl alcohol ethylene oxide-propylene oxide block copolymers, and 2-ethyl hexanol ethylene oxide-propylene oxide block copolymers. Nonlimiting examples of n-butyl alcohol ethylene oxide-propylene oxide block copolymers include Ethylan® NS-500 LQ; non-limiting examples of n-butoxy butyl alcohol ethylene oxide-propylene oxide block copolymers include Atlas® G-5000; and non-limiting examples of 2-ethyl hexanol ethylene oxide -propylene oxide block copolymers include Ecosurf® EH6.

[0022] Particular mixtures of a (Cio-Cis)-fatty alcohol ethoxylate-based surfactant and a (Ci- Cs)-alkyl alcohol ethylene oxide-propylene oxide copolymer-based nonionic surfactant referred to herein are mixtures of (Ci2-Ci5)-fatty alcohol ethoxylate and butanol ethylene oxide-propylene oxide copolymer (such as Atlox® 4894) or mixtures of (Ci2-Ci4)-fatty alcohol ethoxylate and butanol ethylene oxide-propylene oxide copolymer (such as Tersperse® 4894).

[0023] Particular (Cs-Ci8)-alkyl sulfate salt-based surfactants referred to herein are (Cs- Cis)-alkyl sulfate alkali metal salt-based surfactants or (Cs-Ci8)-alkyl sulfate alkaline earth metal salt-based surfactants. Non-limiting examples of (Cs-Ci8)-alkyl sulfate alkali metal salt-based surfactants include lauryl sulfate sodium salt (e.g., Zoharpon® SLS 2000).

[0024] Particular (Cs-C2o)-alkyl benzene sulfonate salt-based surfactants referred to herein are dodecyl benzene sulfonate alkali metal salt-based surfactants or dodecyl benzene sulfonate alkaline earth metal salt-based surfactants. Non- limiting examples of dodecyl benzene sulfonate alkali metal salt-based surfactants include dodecyl benzene sulfonate sodium salt (e.g., Rhodacal® DS-10)

[0025] Particular taurate salt-based surfactants referred to herein are N-(Cn-C2i-CO)-N-(Ci- C4)-alkyl-taurate alkali metal salt-based surfactant or N-(Cn-C2i-CO)-N-(Ci-C4)-alkyl- taurate alkali metal salt-based surfactants. Non-limiting examples of N-(Cn-C2i-CO)-N-(Ci- C4)-alkyl-taurate alkali metal salt-based surfactants include N-oleoyl-N-methyltaurine sodium salt (e.g., Geropon® T 77).

[0026] Particular alkyl naphthalene sulfonate salt-based surfactants referred to herein are (Ci-C6)-alkyl naphthalene sulphonate alkali metal salt-based surfactants or (Ci-C6)-alkyl naphthalene sulphonate alkaline earth metal salt-based surfactants. Non-limiting examples of (Ci-C6)-alkyl naphthalene sulphonate alkali metal salt-based surfactants include diisopropyl naphthalene sulphonate sodium salt (e.g., Supragil® WP) and Morwet® EFW.

[0027] In certain embodiments, the suspended particles of pyroxasulfone comprised within the SC composition of the invention according to any one of the embodiments defined above have a diameter, i.e., D90 value of said particles in the range of from up to about 25, e.g., about 0.5 pm to about 25 pm, from about 1 pm to about 24 pm, from about 1.5 pm to about 23 pm, from about 2 pm to about 22 pm, from about 2.5 pm to about 21 pm, from about 3 pm to about 20 pm, up to about 20 pm, up to about 19 pm, up to about 18 pm, up to about 17 pm, up to about 16 pm, up to about 15 pm, up to about 14 pm, up to about 13 pm, up to about 12 pm, up to about 11 pm, or up to about 10 pm. Particular such embodiments arethose wherein said D90 value does not significantly change, i.e., increase, after storage for long time (e.g., for at least 5 days, at least a week, at least 10 days, or 14 days or more) and / or under elevated temperatures, more specifically the D90 value of said particles is not greater than about 25 pm, e.g., up to about 25 pm, up to about 20 pm, up to about 19 pm, up to about 18 pm, up to about 17 pm, up to about 16 pm, up to about 15 pm, up to about 14 pm, up to about 13 pm, up to about 12 pm, up to about 11 pm, or up to about 10 pm.

[0028] In certain embodiments, the suspended particles of metribuzin comprised within the SC composition of the invention according to any one of the embodiments defined above have a diameter, i.e., D90 value of said particles, in the range of from up to about 25, e.g., about 0.5 pm to about 25 pm, from about 1 pm to about 24 pm, from about 1.5 pm to about 23 pm, from about 2 pm to about 22 pm, from about 2.5 pm to about 21 pm, from about 3 pm to about 20 pm, up to about 20 pm, up to about 19 pm, up to about 18 pm, up to about 17 pm, up to about 16 pm, up to about 15 pm, up to about 14 pm, up to about 13 pm, up to about 12 pm, up to about 11 pm, or up to about 10 pm. Particular such embodiments are those wherein said D90 value does not significantly change, i.e., increase, after storage for long time (e.g., for at least 5 days, at least a week, at least 10 days, or 14 days or more) and / or under elevated temperatures, more specifically the D90 value of said particles is not greater than about 25 pm, e.g., up to about 25 pm, up to about 20 pm, up to about 19 pm, up to about 18 pm, up to about 17 pm, up to about 16 pm, up to about 15 pm, up to about 14 pm, up to about 13 pm, up to about 12 pm, up to about 11 pm, or up to about 10 pm.

[0029] In certain embodiments, the suspended particles of pyroxasulfone comprised within the SC composition of the invention according to any one of the embodiments defined above have a diameter, i.e., D90 value of said particles in the range of from up to about 25, e.g., about 0.5 pm to about 25 pm, from about 1 pm to about 24 pm, from about 1.5 pm to about 23 pm, from about 2 pm to about 22 pm, from about 2.5 pm to about 21 pm, from about 3 pm to about 20 pm, up to about 20 pm, up to about 19 pm, up to about 18 pm, up to about 17 pm, up to about 16 pm, up to about 15 pm, up to about 14 pm, up to about 13 pm, up to about 12 pm, up to about 11 pm, or up to about 10 pm.; and the suspended particles of metribuzin comprised within the SC composition of the invention according to any one of the embodiments defined above have a diameter, i.e., D90 value of said particles in the range of from up to about 25, e.g., about 0.5 pm to about 25 pm, from about 1 pm to about 24 pm, from about 1.5 pm to about 23 pm, from about 2 pm to about 22 pm, from about 2.5 pm to about 21 pm, from about 3 pm to about 20 pm, up to about 20 pm, up to about 19 pm, up toabout 18 pm, up to about 17 pm, up to about 16 pm, up to about 15 pm, up to about 14 pm, up to about 13 pm, up to about 12 pm, up to about 11 pm, or up to about 10 pm.. Particular such embodiments are those wherein said D90 values does not significantly change, i.e., increase, after storage for long time (e.g., for at least 5 days, at least a week, at least 10 days, or 14 days or more) and / or under elevated temperatures (e.g., above room temperature such as at 54°C), more specifically the D90 value of said particles is not greater than about 25 pm, e.g., up to about 25 pm, up to about 20 pm, up to about 19 pm, up to about 18 pm, up to about 17 pm, up to about 16 pm, up to about 15 pm, up to about 14 pm, up to about 13 pm, up to about 12 pm, up to about 11 pm, or up to about 10 pm.

[0030] The term “significantly change” as used herein with respect the D90 value of pyroxasulfone / metribuzin particles refers to a possible increase in the D90 value of said particles after storage, for long time (e.g., for at least 5 days, at least a week, at least 10 days, or 14 days or more) and / or under elevated temperatures (e.g., above room temperature such as at 54°C), of the SC compositions of the invention which is not greater than about 25 pm, e.g., up to about 25 pm, up to about 20 pm, up to about 19 pm, up to about 18 pm, up to about 17 pm, up to about 16 pm, up to about 15 pm, up to about 14 pm, up to about 13 pm, up to about 12 pm, up to about 11 pm, or up to about 10 pm.

[0031] The term “elevated temperature” as used herein refers to a temperature value which higher than room temperature, e.g., higher than 25°C, higher than 30°C, higher than 40°C, or 54°C.

[0032] In certain embodiments, the SC composition of the invention according to any one of the embodiments above further comprises at least one, e.g., one, two, three, four, or more, agriculturally acceptable excipient(s). The term “agriculturally acceptable excipient” as used herein refers to an essentially inert substance that can be used as a diluent and / or carrier for an active agent in a composition for treatment of plants and / or plant parts. Non-limiting examples of agriculturally acceptable excipients include an anti-freeze agent, a dispersant, a preservative (e.g., a biocide), an anti-foaming agent, and a thickener.

[0033] The term “anti-freeze agent” as used herein refers to an additive which lowers the freezing point of a water-based liquid.

[0034] Non-limiting examples of anti-freeze agents include propylene glycol; ethylene glycol; urea; glycerine; and an inorganic salt such as sodium chloride, magnesium chloride, calcium chloride, potassium acetate, sodium acetate, ammonium phosphate, ammonium nitrate, and ammonium sulphate.

[0035] The terms “dispersant” or “dispersing agent” are used herein interchangeably and refer a substance, typically a surfactant, that is added to a suspension of solid particles in a liquid to improve the separation of the particles and to prevent their aggregation or agglomeration thereby preventing the settling or clumping of the particles. Non-limiting examples of dispersants include a methyl methacrylate graft copolymer (e.g., Atlox™ 4913), an alkyl naphthalene sulfonate formaldehyde condensate salt (e.g., Morwet® D425), an ethoxylated tristyrylphenol (e.g., Soprophor® TS / 54), a lignosulfonate-based salt (e.g., sodium lignosulfonate), and a poly carboxy late (e.g., POWERBLOX™ D-205 and POWERBLOX™ D-305).

[0036] The term “preservative” as used herein refers to a chemical that is used in preventing spoilage and extending the shelf life of agriculture products, such as an antioxidant, biocide, and thermal stabilizer. According to the literature, without the addition or with an insufficient addition of preservatives, various problems result, mainly due to the growth of microorganisms; development of unpleasant odors; discolorations; pH changes, to which some pesticides are sensitive; changes in the viscosity caused by the degradation of polysaccharide-comprising thickeners; or phase separation / sedimentation of emulsions or suspensions as the result of microbial degradation of surfactants. Non-limiting examples of preservatives include isothiazolinone-based preservatives such as methyl-2H-isothiazol-3- one (MIT), l,2-benzisothiazol-3(2H)-one (BIT; e.g., Proxel® GXL), chlor-2-methyl-2H- isothiazol-3-on (CMIT), formaldehyde, zinc oxide, sodium propionate, and sodium benzoate.

[0037] The terms “anti-foaming agent” or “defoamer” are used herein interchangeably and refer to a chemical agent that is added to a composition so as to prevent, attenuate, or counter foam generation in the composition. Generally, such agents have surface active properties, are insoluble in the foaming medium, easily spreadable on the foamy surface, possess affinity to the air-liquid surface, and destabilize the foam lamellas which rupture the air bubbles and break down the surface foam.

[0038] Non-limiting examples of anti-foaming agents include siloxane-based antifoams such as organopolysiloxanes, e.g., polydimethylsiloxane-based compounds (e.g., SAG™ 1572); a mixture of alkenes, C11-C12, hydroformylation products, low boiling, or a commercially available product comprising it such as Geronol AF 80; a mineral oil-based defoamer or a commercially available product comprising it such as Lucrafoam® PDT; a blend of special wax, hydrophobic silica, and mineral oil or a commercially available productcomprising it such as DEE FO® 3010E / 50; a silicon emulsion or a commercially available product comprising it such as Silfoam® SE 47, Silfoam® SRE, Silcolapse® RG 12, and SAG 10E; and a silicone-based compound or a commercially available product comprising it such as Silcolapse™ 910, Xiameter™ ACP-1500, and Xiameter® ACP-1000.

[0039] The terms “thickening agent” or “thickener” are used here interchangeably and refer to an additive that is added to an agrochemical formulation to increase its viscosity and prevent sedimentation of the active ingredient(s), thereby conferring greater stability and allowing storage thereof for a longer period.

[0040] Non-limiting examples of thickening agents include starch, dextrin, cellulose, methyl cellulose, ethyl cellulose, carboxymethyl cellulose, hydroxyethyl cellulose, hydroxypropyl cellulose, carboxymethyl starch, pullulan, sodium alginate, ammonium alginate, propylene glycol alginate, guar gum, locust bean gum, Arabic gum, xanthan gum, diutan gum, gelatin, casein, polyvinyl alcohol, polyethylene oxide, polyethylene glycol, a block polymer of ethylene and propylene, sodium polyacrylate, polyvinyl pyrrolidone, and carrageenan.

[0041] In certain embodiments, disclosed herein is a SC composition comprising pyroxasulfone and metribuzin in the form of suspended particles; a surfactant as defined hereinabove; an anti-freeze agent; an anti-foaming agent; at least one dispersant; a thickener; water; and optionally a biocide, wherein each one of said anti-freeze agent; anti-foaming agent; dispersant; thickener; and biocide, is as defined hereinabove.

[0042] Particular such SC compositions comprise (i) pyroxasulfone and metribuzin in the form of suspended particles; (ii) a dialkyl sulfosuccinate salt-based surfactant such as sodium dioctyl sulfosuccinate (e.g., Aerosol® OT-75 PG and Aerosol® OT-100) as a surfactant; (iii) propylene glycol as an anti-freeze agent; (iv) xanthan gum as a thickener; (v) a silicone- based compound (e.g., XIAMETER™ ACP-1500) as an anti-foaming agent; (vi) a combination of a methyl methacrylate graft copolymer (e.g., Atlox™ 4913), an alkyl naphthalene sulfonate formaldehyde condensate salt (e.g., Morwet® D425), and an ethoxylated tristyrylphenol (e.g., Soprophor® TS / 54) as a dispersant; and (vii) water.

[0043] Other particular such SC compositions comprise: (i) pyroxasulfone and metribuzin in the form of suspended particles; (ii) a combination of: (a) an alkyl naphthalene sulfonate salt-based surfactant (such as diisopropyl naphthalene sulphonate sodium salt, e.g., Supragil® WP; and Morwet® EFW), and (b) one of: (bl) a mixture of (Ci2-Cis)-fatty alcohol ethoxylate and butanol ethylene oxide -propylene oxide copolymer (such as Atlox® 4894), (b2) an n-butyl alcohol ethylene oxide -propylene oxide block copolymer (e.g., Ethylan® NS-500 LQ), (b3) (Cio-Cis)-fatty alcohol ethoxylate-based surfactant is a (Ci2-Ci5)-alcohol ethoxylate (e.g., BIO-SOFT® N25-12 and iso-tridecyl alcohol ethoxylate such as Genapol® X-080), (b4) 2-ethyl hexanol ethylene oxide-propylene oxide block copolymer (e.g., Ecosurf® EH6), and (b5) a mixture of (Ci2-Ci4)-fatty alcohol ethoxylate and butanol ethylene oxide-propylene oxide copolymer (such as Tersperse® 4894), as a surfactant; (iii) propylene glycol as an anti-freeze agent; (iv) xanthan gum as a thickener; (v) a silicon emulsion (e.g., SAG™ 1572) as an anti-foaming agent; (vi) an isothiazolinone-based preservative (e.g., PROXEL™ GXL, i.e., a 20% aqueous dipropylene glycol solution of 1,2-benzisothiazolin- 3-one) as a biocide; (vii) a combination of a methyl methacrylate graft copolymer (e.g., Atlox™ 4913) and an alkyl naphthalene sulfonate formaldehyde condensate salt (e.g., Morwet® D425), as a dispersant; and (viii) water.

[0044] In certain embodiments, the wetting agent comprised within the SC composition of the present invention according to any one of the embodiments above constitutes from about 0.01% to about 10%, preferably from about 0.015% to about 8%, from about 0.02% to about 5%, from about 0.025% to about 2%, or from about 0.03% to about 1%, by weight of said composition. Particular such embodiments are those wherein said wetting agent is: (i) a dialkyl sulfo succinate salt-based surfactant such as sodium dioctyl sulfosuccinate (e.g., Aerosol® OT-75 PG and Aerosol® OT-B 100) and it constitutes from about 0.025% to about 2%, preferably from about 0.03% to about 1%, by weight of said composition; (ii) a (Cs- C2o)-alkyl benzene sulfonate salt-based surfactant such as dodecyl benzene sulfonate sodium salt (e.g., Rhodacal® DS- 10) and it constitutes from about 0.025% to about 2%, preferably from about 0.03% to about 1%, by weight of said composition; (iii) an alkyl naphthalene sulfonate salt-based surfactant (such as diisopropyl naphthalene sulphonate sodium salt, e.g., Supragil® WP; and Morwet® EFW) and it constitutes from about 0.025% to about 2%, preferably from about 0.03% to about 1%, by weight of said composition; (iv) a (Cs-Cis)- alkyl sulfate salt-based surfactant such as lauryl sulfate sodium salt (e.g., Zoharpon® SLS 2000) and it constitutes from about 0.025% to about 2%, preferably from about 0.03% to about 1%, by weight of said composition; (v) a taurate salt-based surfactant such as N- oleoyl-N-methyltaurine sodium salt (e.g., Geropon® T 77) and it constitutes from about 0.025% to about 2%, preferably from about 0.03% to about 1%, by weight of said composition; (vi) a (Cio-Cis)-fatty alcohol ethoxylate-based surfactant such as a (C12-C15)- alcohol ethoxylate (e.g., iso-tridecyl alcohol ethoxylate such as Genapol® X-080) and it constitutes from 0.035% to about 0.5%, preferably from about 0.04% to about 0.2%, byweight of said composition; (vii) a (Ci-Cs)-alkyl alcohol ethylene oxide -propylene oxide copolymer-based nonionic surfactant such as an n-butyl alcohol ethylene oxide-propylene oxide block copolymer (e.g., Ethylan® NS-500 LQ) or 2-ethyl hexanol ethylene oxidepropylene oxide block copolymer (e.g., Ecosurf® EH6), and it constitutes from 0.035% to about 0.5%, preferably from about 0.04% to about 0.2%, by weight of said composition; (viii) a mixture of a (Cio-Cis)-fatty alcohol ethoxylate -based surfactant and a (Ci-Cs)-alkyl alcohol ethylene oxide-propylene oxide copolymer-based nonionic surfactant such as a mixture of (Ci2-Cis)-fatty alcohol ethoxylate and butanol ethylene oxide-propylene oxide copolymer (such as Atlox® 4894), and a mixture of (Ci2-Ci4)-fatty alcohol ethoxylate and butanol ethylene oxide-propylene oxide copolymer (such as Tersperse® 4894); or (ix) a combination thereof.

[0045] In another aspect, the present invention relates to a method of controlling weed (undesired vegetation) comprising applying to a locus an effective amount of a formulation of the invention as defined in any one of the embodiments above.

[0046] The term "locus" as used herein refers not only to areas where the weed may already be developed, but also to areas where weeds have yet to emerge, and to areas under cultivation. Locus includes the crop and propagation material of the crop (all the generative parts of the crop such as seeds and vegetative plant material such as cuttings and tubers, which can be used for the multiplication of the plant). Examples of propagation material of the crop include seeds, tubers, spores, corms, bulbs, rhizomes, sprouts basal shoots, stolons, buds and other parts of plants, including seedlings and young plants, which could be transplanted after germination or after emergence from soil. Locus also includes the area surrounding the crop and the growing media of the crop, such as soil and crop field.

[0047] In certain embodiments, the locus is a field of crop. The term “crop” (or “plant”) as used herein refers to whole plants, plant organs (e.g., leaves, stems, twigs, roots, trunks, limbs, shoots, fruits, etc.), plant cells, or plant seeds. Non-limiting examples of crops are wheat, soybean, and legumes (e.g., blackgram, beans, lentils, peas, and chickpeas).

[0048] In certain embodiments, the weeds that can be controlled by the method of the present invention include a grassy or broad-leave weed, e.g., Phalaris minor.

[0049] Unless otherwise indicated, all numbers expressing, e.g., amounts or ratios between components, used in this specification, are to be understood as being modified in all instances by the term "about". Accordingly, unless indicated to the contrary, the numericalparameters set forth in this specification are approximations that may vary by up to plus or minus 10% depending upon the desired properties to be obtained by the present invention.

[0050] The invention will now be illustrated by the following non-limiting Examples.EXAMPLESExample 1. Evaluating the ability of certain surfactants to wet both pyroxasulfone and metribuzin.

[0051] Several wetting agents were tested for their ability to wet a mixture of pyroxasulfone and metribuzin. First, a milled powder of pyroxasulfone and metribuzin (weight ratio of 1:3.5, respectively) was prepared. Then, 300 mg of said powder was sprinkled to 40 ml of an aqueous solution of 1% wetter in water, and the time that took for the powder to sink into the solution was measured. The experiments for Supragil® WP and athe mixture of Supragil® WP and Atlox® 4894 were performed using pyroxasulfone and metribuzin in a weight ratio of 1:1, respectively, and 1% solution of Supragil® WP and 1% Atlox® 4894. The results for each wetter are summarized in Table 1.Table 1Example 2. Evaluating the size of particles comprised within the composition in the presence of representative wetting agents from Table 1

[0052] A formulation was prepared as depicted in Table 2 and stored at 54°C for two weeks. In each experiment, a different wetter was added and the D90 value of the particles was measured using a Malvern 3000 Laser Diffraction instrument. A saturated solution of metribuzin was prepared by stirring 5g of metribuzin in 2L of water overnight before filtering the undissolved metribuzin. Measurements were performed using this saturated solution using the following parameters: Obscuration 10-25%, Refractive index of dispersed phase 1.6, Absorption of the dispersed phase 0.01. Red and Blue light measurements had the same parameters. The refractive index of the saturated solution was set to 1.33.

[0053] The results as well as the list of the tested wetters are shown in Table 3.Table 2Table 3Results and discussion

[0054] As shown in Table 1, surfactants selected from a dialkyl sulfosuccinate salt-based surfactant, more specifically Aerosol® OT-100; a (Cio-Cis)-fatty alcohol ethoxylate -based surfactant, more specifically Genapol® X-080; a (Ci-Cs)-alkyl alcohol ethylene oxidepropylene oxide copolymer-based nonionic surfactant, more specifically Ethylan® NS-500 LQ and Ecosurf® EH6; a (Cs-Ci8)-alkyl sulfate salt-based surfactant, more specifically Zoharpon® SLS 2000; d) a (Cs-C2o)-alkyl benzene sulfonate salt-based surfactant, more specifically Rhodacal® DS- 10; a taurate salt-based surfactant, more specifically Geropon® T 77; an alkyl naphthalene sulfonate salt-based surfactant, more specifically Supragil® WP and Morwet® EFW, were able to wet both pyroxasulfone and metribuzin in a short time, more specifically in the range of from 1 sec to 3 minutes. Representative wetting agents were then tested for their ability not to cause crystal growth of particles, along with their capability to wet the mixture of pyroxasulfone and metribuzin. In order to check whether these wetting agents do not cause significant crystal growth of the particles of the active ingredients, a formulation comprising pyroxasulfone and metribuzin according to Table 2 was prepared and stored at 54°C for two weeks and then the size of the particles comprised within the formulations was measured. As shown in Table 3, the tested surfactants did not cause a significant crystal growth of the particles, i.e., particle size of less than 15 pm, more specifically less than 12 pm, at the tested concentrations of said wetting agents (up to about 1% by weight) after storge for long time and elevated temperatures.Example 3. Preparing pyroxasulfone-metribuzin-based SC formulations and evaluating their physicochemical properties

[0055] Pyroxasulfone-metribuzin-based SC formulations were prepared as depicted in Tables 4, 6, and 8, and physicochemical studies have been performed and the results are shown in Tables 5, 7, and 9.Table 4Table 5Table 6Table 7Table 8Table 9Results and discussion

[0056] A formulation comprising pyroxasulfone and metribuzin, wherein the surfactant was a combination of: a mixture of (Ci2-Cis)-fatty alcohol ethoxylate and butanol ethylene oxidepropylene oxide copolymer, more specifically Atlox® 4894; and an alkyl naphthalene sulfonate salt-based surfactant, more specifically Supragil® WP, was stable and no significant crystal growth of particles was observed after storage at 54°C for two weeks (particle size of 10.67 pm; Table 5).

[0057] A formulation comprising pyroxasulfone and metribuzin, wherein the surfactant was a combination of: an alkyl naphthalene sulfonate salt-based surfactant, more specifically Supragil® WP; and an n-butyl alcohol ethylene oxide -propylene oxide block copolymer, more specifically Ethylan® NS-500 LQ, was stable and no significant crystal growth of particles was observed after storage at 54°C for two weeks (particle size of 9.8 pm; Table 7).

[0058] Additional stable formulations comprising pyroxasulfone and metribuzin were prepared wherein the surfactant was a mixture of an alkyl naphthalene sulfonate salt-based surfactant, more specifically Supragil® WP; and one of: (i) a (Ci2-Ci5)-alcohol ethoxylate, more specifically, Genapol® X-080; (ii) 2-ethyl hexanol ethylene oxide -propylene oxide block copolymer, more specifically, Ecosurf® EH6; or (iii) a mixture of (Ci2-Ci4)-fatty alcohol ethoxylate and butanol ethylene oxide-propylene oxide copolymer, more specifically, Tersperse® 4894 (Tables 8-9).REFERENCESNakatani M., Yamaji Y., Honda H., Uchida Y. Development of the novel preemergence herbicide pyroxasulfone. Journal of pesticide science, 2016, 41, 107-112.

Claims

CLAIMS1. A suspension concentrate (SC) composition comprising:(i) pyroxasulfone and metribuzin in the form of suspended particles;(ii) a wetting agent selected from the group consisting of: (a) a dialkyl sulfo succinate salt-based surfactant, (b) an alkoxylate alcohol-based surfactant selected from a (Cio-Cis)-fatty alcohol ethoxylate -based surfactant, a (Ci-Cs)-alkyl alcohol ethylene oxide-propylene oxide copolymer-based nonionic surfactant, and a mixture thereof, (c) a (C5-Ci8)-alkyl sulfate salt-based surfactant, d) a (Cs-C2o)-alkyl benzene sulfonate salt-based surfactant, (e) a taurate salt-based surfactant, (f) an alkyl naphthalene sulfonate salt-based surfactant, and (g) a combination thereof; and(iii) water.

2. The SC composition of claim 1, wherein said dialkyl sulfo succinate salt-based surfactant is a di-(C7-Ci2)alkyl sulfo succinate alkali metal salt-based surfactant or a di-(C?- Ci2)alkyl sulfosuccinate alkaline earth metal salt-based surfactant.

3. The SC composition of claim 2, wherein said dialkyl sulfo succinate salt-based surfactant is a di-(C7-Ci2)alkyl sulfosuccinate alkali metal salt-based surfactant such as sodium dioctyl sulfo succinate (e.g., Aerosol® OT-75 PG and Aerosol® OT-100).

4. The SC composition of claim 1, wherein: (i) said (Cio-Cis)-fatty alcohol ethoxylate- based surfactant is a (Ci2-Ci5)-alcohol ethoxylate (e.g., BIO-SOFT® N25-12 and iso-tridecyl alcohol ethoxylate such as Genapol® X-080); (ii) said (Ci-Cs)-alkyl alcohol ethylene oxidepropylene oxide copolymer-based nonionic surfactant is an n-butyl alcohol ethylene oxidepropylene oxide block copolymer (e.g., Ethylan® NS-500 LQ), an n-butoxy butyl alcohol ethylene oxide -propylene oxide block copolymer (e.g., Atlas® G-5000), or 2-ethyl hexanol ethylene oxide-propylene oxide block copolymer (e.g., Ecosurf® EH6); or (iii) said mixture of a (Cio-Cis)-fatty alcohol ethoxylate -based surfactant and a (Ci-Cs)-alkyl alcohol ethylene oxide-propylene oxide copolymer-based nonionic surfactant is a mixture of (Ci2-Cis)-fatty alcohol ethoxylate and butanol ethylene oxide -propylene oxide copolymer (such as Atlox® 4894) or a mixture of (Ci2-Ci4)-fatty alcohol ethoxylate and butanol ethylene oxidepropylene oxide copolymer (such as Tersperse® 4894).

5. The SC composition of claim 1, wherein said (Cs-Ci8)-alkyl sulfate salt-based surfactant is a (Cs-Ci8)-alkyl sulfate alkali metal salt-based surfactant or a (Cs-Cis)- alkyl sulfate alkaline earth metal salt-based surfactant.

6. The SC composition of claim 5, wherein said (Cs-Ci8)-alkyl sulfate salt-based surfactant is a (Cs-Ci8)-alkyl sulfate alkali metal salt-based surfactant such as lauryl sulfate sodium salt (e.g., Zoharpon® SLS 2000).

7. The SC composition of claim 1, wherein said (Cs-C2o)-alkyl benzene sulfonate saltbased surfactant is a dodecyl benzene sulfonate alkali metal salt-based surfactant or a dodecyl benzene sulfonate alkaline earth metal salt-based surfactant.

8. The SC composition of claim 7, wherein said (Cs-C2o)-alkyl benzene sulfonate saltbased surfactant is a dodecyl benzene sulfonate alkali metal salt-based surfactant such as dodecyl benzene sulfonate sodium salt (e.g., Rhodacal® DS- 10).

9. The SC composition of claim 1, wherein said taurate salt-based surfactant is an N- (Cn-C2i-CO) -(Ci-C4)-alkyl-taurate alkali metal salt-based surfactant or an 7V-(Cn-C2i- CO)-iV-(Ci-C4)-alkyl-taurate alkali metal salt-based surfactant.

10. The SC composition of claim 9, wherein said taurate salt-based surfactant is an N- (Cn-C2i-CO) -(Ci-C4)-alkyl-taurate alkali metal salt-based surfactant such as / V-oleoyl-iV- methyltaurine sodium salt (e.g., Geropon® T 77).

11. The SC composition of claim 1, wherein said alkyl naphthalene sulfonate salt-based surfactant is a (Ci-C6)-alkyl naphthalene sulphonate alkali metal salt-based surfactant or a (Ci-C6)-alkyl naphthalene sulphonate alkaline earth metal salt-based surfactant.

12. The SC composition of claim 11, wherein said alkyl naphthalene sulfonate salt-based surfactant is a (Ci-C6)-alkyl naphthalene sulphonate alkali metal salt-based surfactant (such as diisopropyl naphthalene sulphonate sodium salt, e.g., Supragil® WP; and Morwet® EFW).

13. The SC composition of any one of claims 1-12, wherein the suspended particles of pyroxasulfone and / or metribuzin have a diameter (D90 value of suspended particles) in the range of from about 0.5 pm to about 25 pm, e.g., up to about 20 pm, up to about 19 pm, upto about 18 pm, up to about 17 pm, up to about 16 pm, up to about 15 pm, up to about 14 pm, up to about 13 pm, up to about 12 pm, up to about 11 pm, or up to about 10 pm.

14. The SC composition of claim 1, further comprising an agriculturally acceptable excipient such as an anti-freeze agent, a dispersant, a biocide, an anti-foaming agent, a thickener, or a combination thereof.

15. The SC composition of claim 14, comprising:(i) pyroxasulfone and metribuzin in the form of suspended particles;(ii) a dialkyl sulfosuccinate salt-based surfactant such as sodium dioctyl sulfo succinate (e.g., Aerosol® OT-75 PG and Aerosol® OT-100);(iii) an anti-freeze agent such as propylene glycol;(iv) a thickener such as xanthan gum;(v) an anti-foaming agent such as a silicone-based compound (e.g., XIAMETER™ ACP-1500);(vi) a dispersant selected from the group consisting of a methyl methacrylate graft copolymer (e.g., Atlox™ 4913), an alkyl naphthalene sulfonate formaldehyde condensate salt (e.g., Morwet® D425), an ethoxylated tristyrylphenol (e.g., Soprophor® TS / 54), and a combination thereof; and(vii) water.

16. The SC composition of claim 14, comprising:(i) pyroxasulfone and metribuzin in the form of suspended particles;(ii) a combination of: (a) a mixture of (Ci2-Cis)-fatty alcohol ethoxylate and butanol ethylene oxide-propylene oxide copolymer (such as Atlox® 4894), and (b) an alkyl naphthalene sulfonate salt-based surfactant (such as diisopropyl naphthalene sulphonate sodium salt, e.g., Supragil® WP; and Morwet® EFW);(iii) an anti-freeze agent such as propylene glycol;(iv) a thickener such as xanthan gum;(v) an anti-foaming agent such as a silicon emulsion (e.g., SAG™ 1572);(vi) a biocide such as an isothiazolinone-based preservative (e.g., PROXEL™ GXL, i.e., a 20% aqueous dipropylene glycol solution of l,2-benzisothiazolin-3- one);(vii) a dispersant selected from the group consisting of a methyl methacrylate graft copolymer (e.g., Atlox™ 4913), an alkyl naphthalene sulfonate formaldehyde condensate salt (e.g., Morwet® D425), and a combination thereof; and(viii) water.

17. The SC composition of claim 14, comprising:(i) pyroxasulfone and metribuzin in the form of suspended particles;(ii) a combination of: (a) an n-butyl alcohol ethylene oxide-propylene oxide block copolymer (e.g., Ethylan® NS-500 LQ), and (b) an alkyl naphthalene sulfonate saltbased surfactant (such as diisopropyl naphthalene sulphonate sodium salt, e.g., Supragil® WP; and Morwet® EFW);(iii) an anti-freeze agent such as propylene glycol;(iv) a thickener such as xanthan gum;(v) an anti-foaming agent such as a silicon emulsion (e.g., SAG™ 1572);(vi) a biocide such as an isothiazolinone-based preservative (e.g., PROXEL™ GXL, i.e., a 20% aqueous dipropylene glycol solution of l,2-benzisothiazolin-3- one);(vii) a dispersant selected from the group consisting of a methyl methacrylate graft copolymer (e.g., Atlox™ 4913), an alkyl naphthalene sulfonate formaldehyde condensate salt (e.g., Morwet® D425), and a combination thereof; and(viii) water.

18. The SC composition of claim 14, comprising:(i) pyroxasulfone and metribuzin in the form of suspended particles;(ii) a combination of: (a) (Cio-Cis)-fatty alcohol ethoxylate -based surfactant is a (Ci2-Ci5)-alcohol ethoxylate (e.g., BIO-SOFT® N25-12 and iso-tridecyl alcohol ethoxylate such as Genapol® X-080), and (b) an alkyl naphthalene sulfonate saltbased surfactant (such as diisopropyl naphthalene sulphonate sodium salt, e.g., Supragil® WP; and Morwet® EFW);(iii) an anti-freeze agent such as propylene glycol;(iv) a thickener such as xanthan gum;(v) an anti-foaming agent such as a silicon emulsion (e.g., SAG™ 1572);(vi) a biocide such as an isothiazolinone-based preservative (e.g., PROXEL™ GXL, i.e., a 20% aqueous dipropylene glycol solution of l,2-benzisothiazolin-3- one);(vii) a dispersant selected from the group consisting of a methyl methacrylate graft copolymer (e.g., Atlox™ 4913), an alkyl naphthalene sulfonate formaldehyde condensate salt (e.g., Morwet® D425), and a combination thereof; and(viii) water.

19. The SC composition of claim 14, comprising:(i) pyroxasulfone and metribuzin in the form of suspended particles;(ii) a combination of: (a) 2-ethyl hexanol ethylene oxide-propylene oxide block copolymer (e.g., Ecosurf® EH6), and (b) an alkyl naphthalene sulfonate salt-based surfactant (such as diisopropyl naphthalene sulphonate sodium salt, e.g., Supragil® WP; and Morwet® EFW);(iii) an anti-freeze agent such as propylene glycol;(iv) a thickener such as xanthan gum;(v) an anti-foaming agent such as a silicon emulsion (e.g., SAG™ 1572);(vi) a biocide such as an isothiazolinone-based preservative (e.g., PROXEL™ GXL, i.e., a 20% aqueous dipropylene glycol solution of l,2-benzisothiazolin-3- one);(vii) a dispersant selected from the group consisting of a methyl methacrylate graft copolymer (e.g., Atlox™ 4913), an alkyl naphthalene sulfonate formaldehyde condensate salt (e.g., Morwet® D425), and a combination thereof; and(viii) water.

20. The SC composition of claim 14, comprising:(i) pyroxasulfone and metribuzin in the form of suspended particles;(ii) a combination of: (a) a mixture of (Ci2-Ci4)-fatty alcohol ethoxylate and butanol ethylene oxide -propylene oxide copolymer (such as Tersperse® 4894), and (b) an alkyl naphthalene sulfonate salt-based surfactant (such as diisopropyl naphthalene sulphonate sodium salt, e.g., Supragil® WP; and Morwet® EFW);(iii) an anti-freeze agent such as propylene glycol;(iv) a thickener such as xanthan gum;(v) an anti-foaming agent such as a silicon emulsion (e.g., SAG™ 1572);(vi) a biocide such as an isothiazolinone-based preservative (e.g., PROXEL™ GXL, i.e., a 20% aqueous dipropylene glycol solution of l,2-benzisothiazolin-3- one);(vii) a dispersant selected from the group consisting of a methyl methacrylate graft copolymer (e.g., Atlox™ 4913), an alkyl naphthalene sulfonate formaldehyde condensate salt (e.g., Morwet® D425), and a combination thereof; and(viii) water.

21. The SC composition of any one of claims 1-20, wherein said wetting agent constitutes from about 0.01% to about 10%, preferably from about 0.015% to about 8%, from about 0.02% to about 5%, from about 0.025% to about 2%, from about 0.03% to about 1%, from about 0.035% to about 0.5%; or from about 0.04% to about 0.2%, by weight of said composition.

22. The SC composition of claim 21, wherein said wetting agent is: (i) a dialkyl sulfosuccinate salt-based surfactant such as sodium dioctyl sulfosuccinate (e.g., Aerosol® OT-75 PG and Aerosol® OT-100) and it constitutes from about 0.025% to about 2%, preferably from about 0.03% to about 1%, by weight of said composition; (ii) a (C8-C20)- alkyl benzene sulfonate salt-based surfactant such as dodecyl benzene sulfonate sodium salt (e.g., Rhodacal® DS- 10) and it constitutes from about 0.025% to about 2%, preferably from about 0.03% to about 1%, by weight of said composition; (iii) an alkyl naphthalene sulfonate salt-based surfactant (such as diisopropyl naphthalene sulphonate sodium salt, e.g., Supragil® WP; and Morwet® EFW) and it constitutes from about 0.025% to about 2%, preferably from about 0.03% to about 1%, by weight of said composition; (iv) a (Cs-Cis)- alkyl sulfate salt-based surfactant such as lauryl sulfate sodium salt (e.g., Zoharpon® SLS 2000) and it constitutes from about 0.025% to about 2%, preferably from about 0.03% to about 1%, by weight of said composition; (v) a taurate salt-based surfactant such as A-oleoyl- A-methyltaurine sodium salt (e.g., Geropon® T 77) and it constitutes from about 0.025% to about 2%, preferably from about 0.03% to about 1%, by weight of said composition; (vi) said wetting agent is a (Cio-Cis)-fatty alcohol ethoxylate-based surfactant such as a (C12- Ci5)-alcohol ethoxylate (e.g., iso-tridecyl alcohol ethoxylate such as Genapol® X-080) and it constitutes from 0.035% to about 0.5%, preferably from about 0.04% to about 0.2%, byweight of said composition; (vii) a (Ci-Cs)-alkyl alcohol ethylene oxide -propylene oxide copolymer-based nonionic surfactant such as an n-butyl alcohol ethylene oxide-propylene oxide block copolymer (e.g., Ethylan® NS-500 LQ) or 2-ethyl hexanol ethylene oxidepropylene oxide block copolymer (e.g., Ecosurf® EH6), and it constitutes from 0.035% to about 0.5%, preferably from about 0.04% to about 0.2%, by weight of said composition; (viii) a mixture of a (Cio-Cis)-fatty alcohol ethoxylate -based surfactant and a (Ci-Cs)-alkyl alcohol ethylene oxide-propylene oxide copolymer-based nonionic surfactant such as a mixture of (Ci2-Cis)-fatty alcohol ethoxylate and butanol ethylene oxide-propylene oxide copolymer (such as Atlox® 4894), and a mixture of (Ci2-Ci4)-fatty alcohol ethoxylate and butanol ethylene oxide-propylene oxide copolymer (such as Tersperse® 4894); or (ix) a combination thereof.

23. A method of controlling weed comprising applying to a locus an effective amount of a composition according to any one of claims 1-22.

24. The method of claim 23, wherein said locus is a field of crop.

25. The method of claim 24, wherein said crop is selected from wheat, soybean, and legumes (e.g., blackgram, beans, lentils, peas, and chickpeas).

26. The method of claim 23, wherein said weed is a grassy or broad-leave weed, specifically Phalaris minor.