AU2015100772A4 - Herbicidal composition comprising propanil and cyhalofop - Google Patents

Abstract

Abstract A composition comprising a synergistic herbicidally effective amount of propanil and cyhalofop in a weight ratio of about 1 . 0.1 - 0.3, preferably 1 . 0.2. The composition is 5 particularly useful for protecting rice crops against undesired weeds.

Description

1 Herbicidal composition comprising Propanil and Cyhalofop Disclosed herein is a composition comprising a synergistic herbicidally effective 5 amount of propanil and cyhalofop in a weight ratio of about 1 : 0.1 - 0.3. The composition is particularly useful for protecting rice crops against undesired weeds. Background Propanil (N-(3,4-Dichlorophenyl)propanamide) is a known broad spectrum grass, 0 broad-leaf (dicotyledonous) and narrow-leaf (monocotyledonous) contact herbicide. It belongs to the group of anilide and controls plant growth by inhibiting their photosynthesis at photosystem II receptor site. Some culture plants such as rice are tolerant to propanil because of the presence of a high level of aryl acylamidase that catalytically degrades the compound to non-phytotoxic products. Propanil is thus typically used in rice cultivation. Over the years 5 biotypes of barnyardgrass and junglerice were discovered to be resistant to propanil. The resistance mechanism of these two biotypes has been shown to be elevated levels of aryl acylamidase activity. Various strategies to combat propanil resistance have been investigated, among them interactions of further herbicides and other chemicals with propanil. One suggested strategy is the combination of propanil and cyhalofop. 0 Cyhalofop ((R)-2-[4-(4-cyano-2-fluorophenoxy)phenoxy]propionic acid) belongs to the herbicide class of ACCase inhibitors effective against grasses. ACCase inhibitors inhibit the enzyme acetyl-CoA carboxylase (ACCase), the enzyme catalyzing the first committed step in fatty acid synthesis. Inhibition of fatty acid synthesis presumably blocks the production of phospholipids used in building new membranes required for cell growth. Broadleaf species 25 are naturally resistant to these herbicides because of an insensitive ACCase enzyme. Hence, the advantage of the use of ACCase inhibitors lies in the fact that the growth of grasses is effectively controlled, whereas the growth of dicotyledonous plants is not affected. Herbicidal compositions comprising both propanil and cyhalofop have been recently reported. For example, US 7,560,416 discloses a composition comprising a propanil-based 30 product and at least one ACCase inhibitor such as cyhalofop. The weight ratio is indicated to range from 1:0.009 propanil-based herbicide to cyhalofop to 1:0.04. When applying the 2 composition comprising propanil-based herbicide and the ACCase inhibitor to rice crops it is reported that compared to traditional compositions not including the ACCase inhibitor 20 % lower amounts of propanil based herbicide is required to facilitate herbicidal activity. US 7,846,873 also discloses a herbicidal composition comprising a propanil-based 5 product and at least one ACCase inhibitor such as cyhalofop in a weight ratio of 1 : 0.009 0.04. Identical conclusions as in US 7,560,416 are drawn, i.e. an improved effect of the combination of both herbicides in the disclosed weight ratio. The combinatorial compositions comprising propanil and cyhalofop of the cited prior art are disclosed to be effective e.g. against barnyard grass (Echinochloa spec.), also known 0 as cockspur (or cockspur grass), barnyard millet, Japanese millet, water grass, and common barnyard grass. Barnyard grass reduces crop yields and causes forage crops to fail by removing up to 80% of the available soil nitrogen and is thus considered one of the world's worst weeds. However, even the combinatorial compositions of the prior art fail to effectively reduce pest growth. 5 Thus, there remains an unmet need for effective herbicidal compositions, in particular for herbicidal compositions to be used in rice cultures. Summary In order to satisfy this need, provided herein is a herbicidal composition comprising a 0 synergistic amount of propanil and cyhalofop. The composition is characterized by a weight ratio of propanil to cyhalofop of about 1 : 0.1-0.3. Thus, according to a first aspect, provided herein is a herbicidal composition comprising propanil and cyhalofop in a weight ratio of about 1 : 0.1-0.3., preferably 1 0.15-0.25, more preferably 1 : 0.17-0.23, even more preferred 1 : 0.18-0.22, more 25 preferably 1 : 0.19-0.21, and most preferred 1 : 0.2. The composition contains one or more agriculturally acceptable adjuvants and/or carriers. The composition may also comprise one or more additional herbicides. The composition may also comprise one or more fungicides, insecticides, nematicides, 30 growth factor enhancers and/or one or more fertilizers.

3 The composition may be formulated in liquid or solid form. The herbicidal composition comprises propanil and cyhalofop in a weight ratio of about 1 . 0.1-0.3, and may further comprise tristyrylphenol ethoxylate, sodium lignosulfonate, and silicone oil. Preferably, said composition further comprises propylene 5 glycol and carboxymethylcellulose. Propanil and cyhalofop may be present in a herbicidal composition in an amount of about 35% by weight propanil and about 3.5 % - 10.5 %, preferably 7% by weight cyhalofop. Also provided herein is a herbicidal composition for use in protecting crops. Preferably 0 the herbicidal composition is used for protecting rice. The composition is preferably applied at 8, 15 or 20 days after seeding of the crop. Also provided herein are methods for controlling undesirable vegetation. These methods comprise applying a herbicidal composition comprising propanil and cyhalofop in a weight ratio as indicated above. Preferably, the undesirable vegetation includes species from 5 the families of Echinochloa, Leptochloa, Ischaemum, Monochoria, and Cyperus, or combinations thereof Accordingly also provided herein is a method for producing a herbicidal composition. The method comprises: providing propanil and cyhalofop, and mixing propanil and cyhalofop in a weight ratio as indicated above. The method preferably further comprises the 0 step of adding one or more agriculturally acceptable adjuvants and/or carriers, one or more surface active agents and/or additives, and/or one or more additional herbicides. Also provided herein is a kit comprising propanil and cyhalofop in separate containers. The kit further comprises instructions for mixing propanil and cyhalofop to obtain a mixture having a weight ratio of propanil to cyhalofop as indicated above. 25 Detailed description A herbicidally effective amount is an amount of herbicide necessary to arrest weed growth, when the herbicide is applied to the weeds. The herbicidal activity is usually exhibited by the compositions when being applied directly to the plant or to the locus of the 30 plant at any stage of growth. The present inventor has surprisingly found out that a weight ratio of propanil to 4 cyhalofop of about 1 : 0.1 to about 1: 0.3 provides a surprising synergistic effect hitherto not reported. Accordingly, provided herein is a herbicidal composition comprising propanil and cyhalofop in a weight ratio of about 1 : 0.1-0.3. The herbicidal composition contains one or more agriculturally acceptable 5 adjuvants/additives and/or carriers. Agriculturally acceptable adjuvants include, but are not limited to, antifreeze agents, antifoam agents, compatibilizing agents, sequestering agents, neutralizing agents and buffers, corrosion inhibitors, colorants or dyes, odorants, penetration aids, wetting agents, spreading agents, sticking agents, dispersing agents, thickening agents, freezing point depressants, 0 antimicrobial agents, crop oil, safeners, adhesives (for instance, for use in seed formulations), surfactants, protective colloids, emulsifiers, tackifiers, extenders, carriers, solvents, stabilizers, preservatives, antioxidants, lubricants, anticaking agents, deformers and diluents and mixtures thereof Exemplary agriculturally acceptable adjuvants include, but are not limited to, crop oil concentrate (mineral oil (85%) + emulsifiers (15%)), nonylphenol 5 ethoxylate, benzylcocoalkyldimethyl quaternary ammonium salt, and blends of petroleum hydrocarbon, alkyl esters, organic acid, and anionic surfactant. A particularly preferred dispersing or wetting agent is tristyrylphenol ethoxylate. A particularly preferred thickening agent is carboxymethylcellulose. Carriers in this respect may be liquid or solid carriers. Liquid carriers that can be 0 employed include water and organic solvents. The organic solvents include, but are not limited to, petroleum fractions or hydrocarbons such as mineral oil, aromatic solvents, paraffinic oils, and the like; vegetable oils such as soybean oil, rapeseed oil, olive oil, castor oil, sunflower seed oil, coconut oil, corn oil, cottonseed oil, linseed oil, palm oil, peanut oil, safflower oil, sesame oil, tung oil and the like; esters of the above vegetable oils; esters of 25 monoalcohols or dihydric, trihydric, or other lower polyalcohols (4-6 hydroxy containing), such as 2-ethyl hexyl stearate, n-butyl oleate, isopropyl myristate, propylene glycol dioleate, di-octyl succinate, di-butyl adipate, di-octyl phthalate and the like; esters of mono, di and polycarboxylic acids and the like. Specific organic solvents include, but are not limited to toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethyl ketone, cyclohexanone, 30 trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butyl acetate, propylene glycol monomethyl ether and diethylene glycol monomethyl ether, methyl alcohol, ethyl 5 alcohol, isopropyl alcohol, amyl alcohol, ethylene glycol, propylene glycol, glycerine, N methyl-2-pyrrolidinone, N,N-dimethyl alkylamides, and dimethyl sulfoxide. In certain embodiments, water is the carrier for the dilution of concentrates. A preferred liquid carrier is silicone oil. A preferred organic solvent is propylene glycol. Suitable solid carriers 5 include but are not limited to talc, pyrophyllite clay, silica, attapulgus clay, kaolin clay, kieselguhr, chalk, diatomaceous earth, lime, calcium carbonate, bentonite clay, Fuller's earth, cottonseed hulls, wheat flour, soybean flour, pumice, wood flour, walnut shell flour, lignin, cellulose, and the like. The composition may comprise one or more inert fillers. Such inert fillers are known 0 in the art and available commercially. Suitable fillers include, for example, natural ground minerals, such as kaolins, aluminas, talc, chalk, quartz, attapulgite, montmorillonite, and diatomaceous earth, or synthetic ground minerals, such as highly dispersed silicic acid, aluminum oxide, silicates, and calcium phosphates and calcium hydrogen phosphates. Suitable inert fillers for granules include, for example, crushed and fractionated natural 5 minerals, such as calcite, marble, pumice, sepiolite, and dolomite, or synthetic granules of inorganic and organic ground materials, as well as granules of organic material, such as sawdust, coconut husks, corn cobs, and tobacco stalks. The composition may optionally include one or more surfactants which are preferably non-ionic, cationic and/or anionic in nature and surfactant mixtures which have good 0 emulsifying, dispersing and wetting properties, depending upon the active compound/compounds being formulated. Suitable surfactants are known in the art and are commercially available. Suitable anionic surfactants can be both so-called water-soluble soaps and water soluble synthetic surface-active compounds. Soaps which may be used include the alkali 25 metal, alkaline earth metal or substituted or unsubstituted ammonium salts of higher fatty acid (CIO to C 2 2 ), for example the sodium or potassium salt of oleic or stearic acid, or of natural fatty acid mixtures. The surfactant may comprise an emulsifier, dispersant or wetting agent of ionic or nonionic type. Examples of such agents include salts of polyacrylic acids, salts of 30 lignosulphonic acid, salts of phenylsulphonic or naphthalenesulphonic acids, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty 6 amines, substituted phenols, especially alkylphenols, sulphosuccinic ester salts, taurine derivatives, especially alkyltaurates, and phosphoric esters of polyethoxylated phenols or alcohols. The presence of at least one surfactant is generally required when the active compound 5 and/or the inert carrier and/or auxiliary/adjuvant are insoluble in water and the vehicle for the final application of the composition is water. The composition may optionally further comprise one or more polymeric stabilizers. Suitable polymeric stabilizers that may be used include, but are not limited to, polypropylene, polyisobutylene, polyisoprene, copolymers of monoolefins and diolefins, 0 polyacrylates, polystyrene, polyvinyl acetate, polyurethanes or polyamides. Suitable stabilizers are known in the art and commercially available. The surfactants and polymeric stabilizers mentioned above are generally believed to impart stability to the composition, in turn allowing the composition to be formulated, stored, transported and applied. 5 Suitable anti-foaming agents for use in the compositions include all substances which can normally be used for this purpose in agrochemical compositions. Suitable anti-foaming agents are known in the art and are available commercially. Particularly preferred antifoam agents are mixtures of polydimethylsiloxanes and perfluroalkylphosphonic acids, such as the silicone anti-foaming agents available from GE or Compton. 0 Suitable solvents for use in the compositions may be selected from all customary organic solvents which thoroughly dissolve the active compounds employed. Again, suitable organic solvents for flufenacet and florasulam are known in the art. The following may be mentioned as being preferred: N-methyl pyrrolidone, N-octyl pyrrolidone, cyclohexyl-1 pyrrolidone; and a mixture of paraffinic, isoparaffinic, cycloparaffinic and aromatic 25 hydrocarbons (available commercially as SOLVESSOTm200). Suitable solvents are commercially available. Suitable preservatives include all substances which can normally be used for this purpose in agrochemical compositions of this type and again are well known in the art. Suitable examples that may be mentioned include PREVENTOL@ (from Bayer AG) and 30 PROXEL@ (from Bayer AG). The compositions may comprise an antioxidant. Suitable antioxidants are all 7 substances which can normally be used for this purpose in agrochemical compositions, as is known in the art. Preference is given to butylated hydroxytoluene. Suitable thickeners for use in the compositions include all substances which can normally be used for this purpose in agrochemical compositions. Examples include xanthan 5 gum, PVOH, cellulose and its derivatives, clay hydrated silicates, magnesium aluminium silicates or a mixture thereof Again, such thickeners are known in the art and available commercially. The compositions may further comprise one or more solid adherents. Such adherents are known in the art and available commercially. They include organic adhesives, including 0 tackifiers, such as celluloses of substituted celluloses, natural and synthetic polymers in the form of powders, granules, or lattices, and inorganic adhesives such as gypsum, silica, or cement. Particularly preferred additives are sodium lignosulfonate and N-methylpyrrolidone. Particularly preferably the composition comprises propanil and cyhalofop in a weight 5 ratio of 1:0.2, tristyrylphenol ethoxylate, sodium lignosulfonate, and silicone oil. Preferably, said compositions further comprise propylene glycol and carboxymethylcellulose. Particularly preferred are amounts of about 35% by weight propanil and about 7% by weight cyhalofop in the compositions. A particularly preferred composition comprises 350g propanil, 70g cyhalofop, 50g 0 tristyrylphenol ethoxylates, lOg sodium lignosulfonate, and lOg silicone oil. To balance to 1 liter N-methylpyrrolidone is added. A further particularly preferred composition comprises 350g propanil, 70g cyhalofop, 100g propylene glycol, 1Og tristyrylphenol ethoxylates, 20g sodium lignosulfonate, 20g carboxymethylcellulose, and 1Og silicone oil. To balance to 1 liter water is added. 25 The compositions can be applied in conjunction with one or more other herbicides to control a wider variety of undesirable vegetation. Thus, when used in conjunction with other herbicides, the composition comprising the other herbicide can be formulated with the other herbicide(s), tank mixed with the other herbicide(s) or applied sequentially with the other herbicide(s). Suitable additional herbicides include, but are not limited to, urea herbicides, 30 uracil herbicides, triazolopyrimidine herbicides, triazolone herbicides, triazole herbicides, triazinone herbicides, triazine herbicides, thiourea herbicides, thiocarbonate herbicides, 8 thiocarbamate herbicides, quaternary ammonium herbicides, pyrimidinyloxybenzylamine herbicides, pyrimidinediamine herbicides, pyridine herbicides, pyridazinone herbicides, pyridazine herbicides, pyrazole herbicides, phenylenediamine herbicides, phenoxy herbicides, oxazole herbicides, oxadiazolone herbicides, organophosphorus herbicides, nitrile 5 herbicides, inorganic herbicides, imidazolinone herbicides, halogenated aliphatic herbicides, fumigant herbicides, dithiocarbamate herbicides, diphenyl ether herbicides, dinitrophenol herbicides, dinitroaniline herbicides, dicarboximide herbicides, cyclopropylisoxazole herbicides, cyclohexene oxime herbicides, carbonate herbicides, carbamate herbicides, benzothiazole herbicides, benzofuranyl alkylsulfonate herbicides, benzoylcyclohexanedione 0 herbicides, arsenical herbicides, aromatic acid herbicides, amide herbicides. The composition can also be applied in conjunction with one or more fungicides, insecticides, nematicides, growth factor enhancers and/or one or more fertilizers. Thus, when used in conjunction with one or more fungicides, insecticides, nematicides, growth factor enhancers and/or one or more fertilizers, the composition may comprise the one or more 5 fungicides, insecticides, nematicides, growth factor enhancers and/or one or more fertilizers or may be formulated such that the composition comprising the herbicides in the inventive ratio is applied before, at the same time or after the one or more fungicides, insecticides, nematicides, growth factor enhancers and/or one or more fertilizers. The composition may contain the two herbicides propanil and cyhalofop in numerous 0 different physical forms such as solid or liquid form. For example, water-soluble concentrates (SL), emulsifiable concentrates (EC), emulsions (EW), micro-emulsions (ME), suspension concentrates (SC), oil-based suspension concentrates (OD), flowable suspensions (FS), water-dispersible granules (WG), water-soluble granules (SG), water-dispersible powders (WP), water soluble powders (SP), granules (GR), encapsulated granules (CG), fine 25 granules (FG), macrogranules (GG), aqueous suspo-emulsions (SE), capsule suspensions (CS) and microgranules (MG). Alternatively, readily prepared compositions such as premixes containing the two herbicides can be provided. Typical liquid compositions include emulsions, suspensions (including suspensions containing microcapsules), solutions, emulsifiable concentrates, and flowables. Preferred is an emulsifiable concentrate (EC) 30 containing both herbicides in the respective ratio, or a two-phase emulsion (or microemulsion) with one herbicide in each phase. Particularly suitable forms of the 9 composition are emulsifiable concentrates (EC) and suspension concentrates (SC), the general formulation of which is known to the person skilled in the art. Particularly preferred is a liquid formulation that can be applied by way of coating, spraying, sprinkling, dipping, soaking, injection or irrigation. In a liquid formulation propanil is preferably present in an 5 amount of about 350g/l and cyhalofop in an amount of about 70g/l. Other amounts are also encompassed as long as they essentially meet the weight ratio of propanil to cyhalofop of about 1 : 0.1-0.3. An example of a solid product containing both herbicides includes for example impregnated granules. Similarly, other solid formulations such as wettable powders (WP) or 0 dusts can be provided. Alternatively, microencapsulated products in which one or both herbicides are contained within a microcapsule can be provided. The microencapsulated products could be provided in either liquid form (i.e., capsule suspensions) or solid form (i.e., water-dispersible granules produced by drying of microcapsule suspensions). One type of liquid form can be a 5 microcapsule suspension in which one of the herbicides is contained within the capsules while the other is present in a nonencapsulated form, in the continuous liquid phase. The types of formulations or compositions which may contain the two herbicides in the respective weight ratio is not limited by those explicitly mentioned herein. Also provided herein is the herbicidal composition for use in protecting crops. Along 0 with this use, also provided herein are methods for controlling undesirable vegetation such as weeds. These methods comprise applying a herbicidal composition comprising propanil and cyhalofop in a weight ratio of about 1 : 0.1-0.3, preferably 1:0.2. The composition and method provided can be utilized to control weeds or battle undesired vegetation in crops or other settings, including but not limited to cereals, such as wheat, barley, rye, oats, 25 corn/maize, rice, sorghum, triticale and related crops; beet, for example sugar beet and fodder beet; fruit, such as pomes, stone fruit and soft fruit, for example apples, grapes, pears, plums, peaches, almonds, cherries, and berries, for example strawberries, raspberries and blackberries; leguminous plants, for example beans, lentils, peas, soybeans, peanuts; oil plants, for example rape, mustard, sunflowers; cucurbitaceae, for example marrows, 30 cucumbers, melons; fibre plants, for example cotton, flax, hemp, jute; citrus fruit, for example oranges, lemons, grapefruit and mandarins; vegetables, for example spinach, 10 lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes, paprika; as well as ornamentals, such as flowers, shrubs, broad-leaved trees and evergreens, for example conifers, pastures, grasslands, rangelands, fallowland, turf, tree and vine orchards, and industrial vegetation management. Preferably, the undesirable vegetation includes species 5 from the families of broadleaved and grass weeds, more preferably from the families of Aeschynomene, Ageratum, Amaranthus, Bidens, Brachiaria, Cenchrus, Cyperus, Digitaria, Echinochloa, Eclipta, Eleusine, Eragrostis, Fimbristylis, Galinsoga, Ischaemum, Leptochloa, Monochoria, Panicum, Paspalum, Polygonum, Portulaca, Richardia, Sesbania, Setaria, Sida, Sorghum, most preferably Echinochloa, Leptochloa, Ischaemum, Monochoria, and Cyperus, 0 or combinations thereof The compositions and methods are preferably used against Echinochloa crus-galli, Echinochloa colonum, Leptochloa chinensis, Ischaemum rugosum, Monochoria vaginalis, and Cyperus ferax. More preferably, the compositions and methods are used against barnyard grass (Echinochloa cms-galli), red sprangletop (Leptochloa chinensis), and heartleaf false pickerelweed (Monochoria vaginalis). To control the 5 undesirable vegetation and to protect the crops and in particular rice, the composition may be applied prior to planting, after planting but prior to flooding (pre-flood, post-emergence) or after emergence of the rice and flooding (post-flood, post- emergence) and may be applied to either direct seeded (drilled or surface seeded), water seeded or transplanted rice. A particularly preferred method includes applying the composition at 8, 15 or 20 days after 0 seeding. The present compositions can be applied to the undesirable vegetation and/or weeds or their locus by the use of conventional ground or aerial dusters, sprayers, and granule applicators, by addition to irrigation or paddy water, and by other conventional means known to those skilled in the art. 25 Also provided herein is a method for producing a herbicidal composition. The method comprises the steps of: providing propanil and cyhalofop, and mixing propanil and cyhalofop in a weight ratio of about 1 : 0.1-0.3, preferably 1 : 0.2. The composition may be formulated in liquid or solid form. In some cases, a respective composition may be produced by simply physically mixing commercially available products 30 (either liquid or solid, or both) containing the active herbicides, for example, two emulsifiable concentrates containing the herbicides. Respective physical forms of the 11 composition have been described above. In case the herbicidal composition shall comprise further additives, the method also comprises the step of adding one or more of said additives such as the agriculturally acceptable adjuvants and/or carriers, the surface active agents, and/or the additional 5 herbicides, insecticides, nematicides, growth factor enhancers, fertilizers, etc. Also provided herein is a kit comprising the two herbicides propanil and cyhalofop in separate containers. The kit further comprises instructions for mixing the herbicides so as to obtain a mixture having an overall weight ratio of propanil to cyhalofop of about 1 : 0.1-0.3, preferably 1 : 0.2. 0 The specific weight ratio of propanil to cyhalofop of about 1 : 0.1-0.3, preferably 1: 0.2 produces an unexpectedly effective control of weeds especially in rice when applied at various times, and to rice planted in different ways. In general, the application rate of the active ingredients depends on such factors as the type of weed, type of crop plant, soil type, season, climate, soil ecology and various other 5 factors. The application rate of the composition for a given set of conditions can readily be determined by routine trials. In general the composition or the method can be applied at an application rate of from about 0.005 pounds/acre (lb/ac) to about 2 lb/ac of the total amount of propanil and cyhalofop being applied. Preferably, the application rate is from about 0.01 lb/ac to 1.5 lb/ac 0 of propanil and cyhalofop. More preferably, the application rate is from about 0.05 lb/ac to 1 lb/ac of propanil and cyhalofop. The application rate of the active ingredients is up to 1 lb/ac of propanil and from 0.005 lb/ac to 1 lb/ac of cyhalofop. Preferably, the application rate of the active ingredients is from 0.3 lb/ac to 0.6 lb/ac of propanil and from 0.06 lb/ac to 0.12 lb/ac of cyhalofop. 25 Although the present invention has been described with reference to preferred embodiments and examples thereof, the scope is not limited only to those described embodiments. As will be apparent to persons skilled in the art, modifications and adaptations can be made without departing from the spirit and scope, which is defined by the appended claims. 30 Embodiments will now be described, for illustrative purposes only, by way of the following examples.

12 Examples Formulation examples 5 Emulsifiable concentrates (EC) were prepared by mixing propanil, cyhalofop, tristyrylphenol ethoxylates (50 g), sodium lignosulfonate (10 g), silicone oil (10 g) and N methylpyrrolidone (balance to 1 L). For example, 35% Propanil + 7% Cyhalofop EC was prepared by having the following composition: Propanil 350g Cyhalofop 70g Tristyrylphenol ethoxylates 50g Sodium lignosulfonate log Silicone oil 1og N-methylpyrrolidone Balance to IL 0 Suspension concentrates (SC) were prepared by mixing finely ground propanil, finely ground cyhalofop, propylene glycol (100 g), tristyrylphenol ethoxylates (10 g), sodium lignosulfonate (20 g), carboxymethylcellulose (20 g), silicone oil (10 g) and water (balance to IL). 5 For example, 35% Propanil + 7% Cyhalofop SC was prepared by having the following composition: Propanil 350g Cyhalofop 70g Propylene glycol 1 OOg Tristyrylphenol ethoxylates log Sodium lignosulfonate 20g Carboxymethylcellulose 20g Silicone oil 1og Water Balance to IL 20 Biological Examples 1 Rice (Oryza sativa), barley (Hordeum vulgare) and wheat (Triticum spec.) were sown side by side in the field. Different types of weeds and their relative density were recorded 13 and are listed in Table 1 below. Formulations were applied 8 days after seeding. After spraying, the beds were maintained for about 2 weeks. Two weeks after application, the beds were examined to determine the efficiency of the treatment. The results are set forth below in Table 2 below. 5 Table 1. Type of weed Type of weed Relative density % Barnyard grass (Echinochloa crus-galli) 50 Red sprangletop (Leptochloa chinensis) 20 Heartleaf false pickerelweed (Monochoria vaginalis) 30 Table 2. Efficiency (%) Efficiency (%) Active i gredient Type of weed Examples Propanil (lIb/ac) Cyhalofop (lb/ac) Echinochloa crus- Leptochloa Monochoria vaginalis ropai ~)Ia) ~yaop ~c) alli chinensis Untreated 0 0 0 0 0 Example 1 6 0 45 25 25 Example 2 0 0.3 20 45 25 Example 3 0.3 0.3 60 60 45 Example 4 0.3 0.12 80 80 75 Example 5 0.3 0.06 95 95 100 Example 6 0.6 0.12 95 100 100 Example 7 0.6 0.06 90 85 85 Example 8 0.6 0.03 75 80 75 Example 9 1 0.009 60 55 45 Example 10 1 0.02 60 60 50 Example 11 1 0.04 70 65 65 Example 12 2.25 0.042 60 60 55 Example 13 3 0.07 70 75 60 Example 14 4 0.149 80 80 70 Example 15 4 0.037 70 60 50 Example 16 5 0.093 60 60 60 Example 17 6 0.112 60 55 60 10 Biological Examples 2 Rice (Oryza sativa), barley (Hordeum vulgare) and wheat (Triticum spec.) were sown side by side in the field. Different types of weeds and their relative density were recorded and are listed in Table 3 below. Formulations were applied 15 days after seeding. After 15 spraying, the beds were maintained for about 2 weeks. Two weeks after application, the beds were examined to determine the efficiency of the treatment. The results are set forth below in Table 4 below.

14 Table 3. Type of weed Type of weed Relative density (%) Cyperus ferax 25 Echinochloa colonum 25 Barnyard grass (Echinochloa crus-galli) 30 Wrinkle duck beak (Ischaemum rugosum) 10 Red sprangletop (Leptochloa chinensis) 10 Table 4. Efficiency (%) Efficiency (%) Active ingredient Type of weed Examples Propanil Cyhalofop Cyperus Echinochloa Echinochloa Ischaemum Leptochloa (lb/ac) (lb/ac) ferax colonum crus-galli rugosum chinensis Untreated 0 0 0 0 0 0 0 Example | 6 0 25 50 45 45 20 Example 2 0 0.3 50 20 25 45 45 Example 3 0.3 0.3 60 60 65 65 60 Example 4 0.3 0.12 80 80 75 85 75 Example 5 0.3 0.06 100 95 100 100 95 Example 6 0.6 0.12 95 95 100 100 100 Example 7 0.6 0.06 85 85 85 85 85 Example 8 0.6 0.03 80 75 80 80 75 Example 9 1 0.009 60 65 60 65 55 Example 10 1 0.02 65 65 60 65 60 Example 11 1 0.04 70 70 65 70 70 Example 12 2.25 0.042 65 65 60 65 60 Example 13 3 0.07 80 70 70 75 75 Example 14 4 0.149 80 80 80 85 80 Example 15 | 4 0.037 65 65 70 75 55 Example 16 | 5 0.093 60 60 65 | 65 60 Example 17 | 6 0.112 60 65 60 | 65 55 5 Biological Examples 3 Rice (Oryza sativa), barley (Hordeum vulgare) and wheat (Triticum spec.) were sown 10 side by side in the field. Different types of weeds and their relative density were recorded and are listed in Table 5 below. Formulations were applied 20 days after seeding. After spraying, the beds were maintained for about 2 weeks. Two weeks after application, the beds were examined to determine the efficiency of the treatment. The results are set forth below in Table 6 below. 15 15 Table 5. Type of weed Type of weed Relative density (%) Echinochloa colonum 25 Barnyard grass (Echinochloa crus-galli) 20 Wrinkle duck beak (Ischaemum rugosum) 15 Red sprangletop (Leptochloa chinensis) 15 Heartleaf false pickerelweed (Monochoria vaginalis) 25 Table 6. Efficiency (%) Efficiency (%) Active ingredient Type of weed Examples Propanil Cyhalofop Echinochloa Echinochloa Ischaemum Leptochloa Monochoria (lb/ac) (lb/ac) colonum crus-galli rugosum chinensis vaginalis Untreated 0 0 0 0 0 0 0 Example 1 6 0 45 50 45 25 25 Example 2 0 0.3 25 25 50 50 30 Example 3 0.3 0.3 60 65 65 60 45 Example 4 0.3 0.12 80 80 80 80 75 Example 5 0.3 0.06 100 100 100 100 95 Example 6 0.6 0.12 95 95 100 100 95 Example 7 0.6 0.06 80 85 85 85 85 Example 8 0.6 1 0.03 75 70 70 75 75 Example 9 1 | 0.009 65 55 65 55 50 Example 10 1 1 0.02 65 60 65 60 50 Example 11 1 1 0.04 65 65 70 70 65 Example 12 2.25 | 0.042 65 60 70 60 55 Example 13 3 0.07 70 65 80 75 60 Example 14 4 0.149 75 80 85 75 70 Example 15 4 0.037 65 65 75 60 55 Example 16 5 0.093 60 60 65 60 55 Example 17 6 0.112 65 60 70 60 60 5 Throughout the specification and the claims that follow, unless the context requires otherwise, the words "comprise" and variations such as "comprises" and "comprising" will be understood to imply the inclusion of a stated integer or group of integers, but not the exclusion of any other integer or group of integers. The reference to any prior art in this specification is not, and should not be taken as, an 10 acknowledgement of any form of suggestion that such prior art forms part of the common general knowledge.

Claims (5)

1. A herbicidal composition comprising propanil and cyhalofop in a weight ratio of about 1 : 0.1-0.3, and one or more agriculturally acceptable adjuvants and/or carriers. 5

2. The herbicidal composition of claim 1, wherein the weight ratio of propanil to cyhalofop is 1 : 0.2.

3. The herbicidal composition of claim 1 or 2, formulated as an emulsifiable concentrate 0 or suspension concentrate.

4. The herbicidal composition of any one of claims 1 to 3, wherein the concentration of propanil and cyhalofop in the composition is in the range of from 0.0005% to 95 % by weight. 5

5. A method for controlling undesirable vegetation, the method comprising applying a herbicidal composition according to any one of claims 1 to 4 to a plant or a plant part or the locus thereof