Composition comprising pretilachlor and flupyralid with reduced viscosity

Abstract

Disclosed is a composition comprising pretilachlor, flupyralid, and one or more surfactants wherein the composition has a viscosity of less than 600 cp.

Description

[0001] The present invention relates to a composition for controlling plant growth, and to the preparation and use of the composition.

[0002] There is a need for herbicidal compositions suitable for application on rice paddies. However, directly applied formulations, such as suspension concentrates (SC), oil dispersions (OD) or granules (GR) may settle on the rice paddy bed and / or clumps, leading to local phytotoxicity. Such compositions also require a strict water level of at least 5 cm before and after application.

[0003] Aqueous emulsions (EWs) have the benefit that they are easy to make and have good chemical stability, and can be applied directly or diluted to paddy water, and spontaneous emulsification of oil droplets containing one or more active ingredients will cause these oil droplets to float or rise to float and spread over the surface of the field without settling.

[0004] However, EW formulations, especially concentrated EW formulations, typically have high viscosities, which are undesirable for direct pour application into the field and are less aesthetically pleasing to the end user, while low viscosity compositions have difficulty achieving sufficient oil phase concentrations, and in turn, sufficient concentrations of the one or more active ingredients.

[0005] Therefore, in a first aspect of the present invention, there is provided a composition comprising Pretilachlor, Florpyrauxifen and one or more surfactants, wherein the composition has a viscosity of less than 600 cps (centipoise). Preferably, the composition is an aqueous emulsion (EW).

[0006] Advantageously, the composition may have a viscosity of less than 500 cps, 450 cps, 400 cps, or even 350 cps.

[0007] The viscosity is measured with a Brookfield viscometer using a No. 2 rotor and having a rotation speed of 30 rpm.

[0008] The structures of the active ingredients are listed in Table 1.

[0009] Table 1

[0010]

[0011] Advantageously, the oil phase:water phase ratio (φ) is 1.1:1 or higher, such as 1.2:1 or higher, 1.3:1 or higher, 1.4:1 or higher, most preferably 1.5:1 or higher. Higher ratios of the composition allow for the preparation of more concentrated compositions.

[0012] Pretilachlor may preferably be present in an amount of 10 to 50% by weight, such as 12 to 45%, 15 to 42%, 20 to 40%, or even 25 to 35%.

[0013] Flupic acid may preferably be present in an amount of 0.01 to 10% by weight, such as 0.05 to 8%, 0.09 to 7%, preferably 0.1 to 5% by weight, or even 0.5 to 1.5% by weight.

[0014] The one or more surfactants suitable for use in the compositions of the invention include tristyrylphenol ethoxylates, such as Soprophor TS-10 (Rhone Poulenc SA) or BSU (Rhodia Geronazzo Spa); EO / PO / EO block copolymers, such as Pluronic F-108, Pluronic F-38, Pluronic P-105 (BASF Wyandotte Corp.); and / or sodium salts of sulfonated naphthalenesulfonic acid-formaldehyde condensation products, such as Morwet D-425 (Wacker Chem. Corp.) or Orotan SN (Rohm and Haas, France SA); lignin sulfonates; PO / EO butanol copolymers, such as Atlox G-5000; block copolymers of polyhydroxystearic acid and polyalkylene glycol, such as Atlox 4912 or 4914 (American Hoechst); or partially hydrolyzed or fully hydrolyzed polyvinyl acetate, for example Mowiol 18-88 or Mowiol 4-88 (Hoechst AG).

[0015] Particularly preferably, the one or more surfactants are selected from the group comprising polyalkylene glycols (e.g. Atlox 4914), butyl polyalkylene oxide block copolymers (e.g. Toximul 8320), ethoxylated sorbitan esters (e.g. polyoxyethylene (8) sorbitan monolaurate 'Tween 22'), polyoxyethylene tridecyl phosphate (e.g. Rhodalfac RS610E) and anionic acrylic copolymers (e.g. Zephrym PD3315).

[0016] The one or more surfactants are present in a total amount of 1% to 10%, such as 2% to 8%, 2.5% to 7%, or even 2.8% to 6% by weight.

[0017] In particularly preferred embodiments, the one or more surfactants include Atlox 4914, Tween 20 and Toximul 8320.

[0018] Advantageously, the composition may contain xanthan gum. Surprisingly and counter-intuitively, it has been found that xanthan gum acts as a thinning agent in the context of the present invention and is used to reduce viscosity. It may also contribute to forming fine droplets when applied.

[0019] Xanthan gum is preferably present in a non-zero amount, but less than 0.2% by weight, such as less than 0.1%, less than 0.05%, less than 0.01% or even less than 0.005% (e.g., 0.00001% to 0.005% by weight).

[0020] Advantageously, the composition comprises an adjuvant to improve the efficacy of the composition. Preferably, the adjuvant comprises an alkyl methyl ester. The alkyl chain length may be 1 to 30 carbons, such as 5 to 25 carbons, or even 10 to 20 carbons, such as C 18 Methyl oleate ('Agnique ME 181').

[0021] It has also been found that the presence of an adjuvant helps to form fine droplets, such as those having a D of less than 2.5 microns. 95 Those.

[0022] Solvents may be included. Any substantially water-insoluble solvent is suitable as the hydrophobic solvent, for example aromatic solvents from the class of toluene, xylene, alkylbenzenes and alkylnaphthalenes, and also saturated and unsaturated hydrocarbons, aryl-alkyl ketones, esters, fatty acid methyl esters, rapeseed oil, C1-C6 alkyl esters, in particular rapeseed oil methyl ester and rapeseed oil ethyl ester, esters of acetic acid or benzoic acid, amides of alkanecarboxylic acids, linear or cyclic acetates, alkylpyrrolidones, alkylcaprolactones, and also alkyl carbonates or mixtures of these solvents.

[0023] For efficient dispersion on the field, it is advantageous for the density of the oil phase to be less than 1 g / ml. Solvents with a low density are therefore preferred.

[0024] Oil phase stabilizers suitable for use in the composition according to the invention include polymers, copolymers and oligomers or mixtures thereof selected from the class of polystyrene, water-insoluble poly(n-alkylene) glycols (where n>2), polypropylene glycol, polyvinyl acetate and polyvinyl acetate-copolymers.

[0025] The oil phase stabilizer can be:

[0026] 1) Polymers of monoolefins and diolefins.

[0027] 2) Mixtures of the polymers mentioned under 1), mixtures of different types of polyethylene (eg LDPE / HDPE).

[0028] 3) Copolymers of monoolefins and diolefins with each other or with other vinyl monomers.

[0029] 3a) Hydrocarbon resins (eg C5-C9), including hydrogenated modifications thereof.

[0030] 4) Polystyrene, poly(p-methylstyrene), poly(α-methylstyrene).

[0031] 5) Copolymers of styrene or α-methylstyrene with dienes or acrylic derivatives.

[0032] 6) Graft copolymers of styrene or methylstyrene.

[0033] 7) Halogenated polymers.

[0034] 8) Polymer derivatives of α-unsaturated acids and their derivatives.

[0035] 9) Copolymers of the monomers mentioned under 8) with one another or with other unsaturated monomers, for example acrylonitrile / butadiene copolymers, acrylonitrile / alkyl acrylate copolymers, acrylonitrile / alkoxyalkyl acrylate or acrylonitrile / vinyl halide copolymers or acrylonitrile / alkyl methacrylate / butadiene terpolymers.

[0036] 10) Polymers derived from unsaturated alcohols and amines or their acyl derivatives and acetal derivatives; and copolymers thereof with the olefins mentioned under 1).

[0037] 11) Homopolymers and copolymers of cyclic ethers.

[0038] 12) Polyacetals, such as polyoxymethylene and polyoxymethylene containing ethylene oxide as a comonomer.

[0039] 13) Polyphenylene ether and polyphenylene sulfide.

[0040] 14) Polyurethanes derived from polyethers, polyesters and polybutadienes which have terminal hydroxyl groups on the one hand and aliphatic or aromatic polyisocyanates on the other hand.

[0041] 15) Polyamides and copolyamides derived from diamines, dicarboxylic acids and aminocarboxylic acids derived from the corresponding lactams.

[0042] 16) Polyureas, polyimides and polyamide-imides and polybenzimidazoles.

[0043] 17) Polyesters derived from dicarboxylic acids and diols and / or from hydroxycarboxylic acids and their lactones.

[0044] 17a) Polyesters and copolymers thereof derived from aliphatic dicarboxylic acids and diols and / or oligoethers and having the general formula:

[0045] -(OXOC(=O)-YC(O=)) z

[0046] Where X = -(CH2) n -, where n = 2 to 12, or

[0047] X=[-(CH2) n -O-(CH2)n] r , where n=2 to 4, and r=2 to 10,

[0048] Y=-(CH2) m -, wherein m=0 to 12, and z=5 to 100.

[0049] 18) Polycarbonates and polyester carbonates.

[0050] 19) Polysulfone, polyethersulfone and polyetherketone.

[0051] 20) Polyethers of diglycidyl compounds (including diglycidyl ethers and diols).

[0052] 21) Natural polymers (eg rubbers) and chemically modified homologous derivatives of natural polymers, for example cellulose acetate, cellulose propionate and cellulose butyrate, or cellulose ethers, for example methylcellulose (degree of substitution >2.5); and also resins and their derivatives.

[0053] 22) Mixtures of the above polymers.

[0054] 23) Mineral oil, fatty acid alkyl ester or rapeseed oil C 1-6 Alkyl esters.

[0055] The molecular weight of the polymers suitable for the oil phase stabilizers of the composition according to the invention (determined for example by light scattering measurements or by osmotic pressure measurements) may be up to 1 000 000 and is generally between 1000 and 1 000 000 Daltons, preferably between 1000 and 100 000 Daltons. In the case of compounds which are extremely hydrophobic and therefore have very low solubility in water (e.g. alkanes and fatty acid alkyl esters), the Mw may also be less than 1000.

[0056] The oil phase stabilizers are used in the compositions according to the invention in concentrations of 0.5% to 10% by weight, preferably 1% to 5% by weight, based on the entire formulation. In the case of compounds which are extremely hydrophobic and therefore have very low solubility in water (e.g. alkanes and fatty acid alkyl esters) and have a low molecular weight, the concentration of the oil phase stabilizer may be up to 25%.

[0057] Furthermore, substances which lower the melting point of the emulsion, ie which prevent the preparation from freezing at low temperatures (antifreeze agents), may be added to the preparations according to the invention.

[0058] Such substances are generally water-soluble salts suitable for lowering the freezing point of the aqueous phase of the emulsion according to the invention, such as sodium chloride, potassium chloride, ammonium chloride, ammonium nitrate and sodium nitrate and mixtures thereof. Also suitable are water-soluble glycols, such as ethylene glycol, propylene glycol, diethylene glycol, glycerol and mixtures thereof. Salts and glycols are preferably used in a concentration of 0.5 to 10% by weight, based on the overall emulsion formulation, in each case.

[0059] The emulsion according to the invention may additionally contain as adjuvants preservatives (eg Acticide LG) or formaldehyde which inhibit the growth of microorganisms such as bacteria and fungi. Such adjuvants may be used in an amount of 0.1% to 0.5% by weight of the entire formulation.

[0060] In a second aspect of the invention, there is provided a method for preparing a composition as defined herein. The organic phase comprising pretilachlor and clofopyralid may be emulsified in an aqueous phase by a suitable stirrer (e.g. a YSTRALO X 40 / 32 emulsifier with a stirring speed of 3000 to 6000 rpm). Depending on the formulation and speed used, an emulsion having a particle size in the preferred range of 1-10 microns is obtained.

[0061] In a third aspect of the invention, there is provided a method of controlling the growth of undesirable plants, the method comprising applying to the plants or their sites a herbicidally effective amount of a composition as described herein. However, commercial products will preferably be formulated as concentrates, and the end user will typically dilute the composition with water. Advantageously, these compositions are applied to paddy fields.

[0062] In a fourth aspect of the invention, there is provided the use of xanthan gum for reducing the viscosity of an agrochemical composition, preferably wherein the agrochemical composition is an aqueous emulsion. Advantageously, the xanthan gum will be used in the amount and form described above.

[0063] In a fifth aspect of the invention there is provided a combination of an unmanned aerial vehicle and a composition as described herein.

[0064] Unless otherwise stated, percentages are given as percentages by weight of the total and all embodiments and preferred features may be combined in any combination.

[0065] The invention is described by the following non-limiting examples.

[0066] Examples

[0067] The following compositions were prepared.

[0068] Table 2

[0069]

[0070]

[0071] Physical properties

[0072] The viscosity of the composition is:

[0073] Composition 1: 580cps;

[0074] Composition 2: 300 cps; and

[0075] Composition 3: 385cps.

[0076] The measurement was performed using a Brookfield viscometer using a No. 2 spindle and having a rotation speed of 30 rpm.

[0077] Figure 1 A shear rate sweep at 25°C is shown for Composition 2 and demonstrates shear thinning behavior, which is particularly advantageous for direct pour application.

[0078] The role of xanthan gum

[0079] Figure 2 Shown are: left, Composition 2 with 20 ppm xanthan gum added before emulsification; middle, Composition 2 without xanthan gum; right, Composition 2 with 20 ppm xanthan gum added after the emulsification step.

[0080] It can be seen that the addition of xanthan gum unexpectedly results in improved and reduced viscosity compared to the absence of xanthan gum.

[0081] effect

[0082] The herbicidal activity of the composition was tested against barnyardgrass (Echinochloa crus-galli) (ECHCG) by spraying or foliar application. Composition 2 was mixed with the commercially available herbicide Topshot TM (containing the active ingredients penoxsulam and cyhalofop) for comparative testing.

[0083] The results are shown in Table 3.

[0084] Table 3

[0085]

[0086] It can also be seen that the compositions according to the invention have improved performance relative to commercial compositions in terms of efficacy against significant weeds.

[0087] The invention is defined by the claims.

Claims

1. A composition comprising pretilachlor, clofopyralid and one or more surfactants, wherein the composition has a viscosity of less than 600 cps.

2. The composition according to claim 1, wherein The composition is an aqueous emulsion (EW).

3. The composition according to claim 1, wherein The oil phase:water phase ratio (φ) is 1.1:1 or higher, preferably 1.5:1 or higher.

4. A composition according to any one of the preceding claims, wherein The pretilachlor is present in an amount of 20 to 40% by weight.

5. A composition according to any one of the preceding claims, wherein The fluopicolide is present in an amount of 0.1% to 5% by weight.

6. A composition according to any one of the preceding claims, wherein The one or more surfactants are selected from the group consisting of polyalkylene glycols, butyl polyalkyleneoxy block copolymers, ethoxylated sorbitan esters, polyoxyethylene tridecyl phosphate, and anionic acrylic copolymers.

7. A composition according to any preceding claim, comprising xanthan gum, preferably in an amount less than 0.2% by weight.

8. A composition according to any one of the preceding claims, comprising an adjuvant, preferably an adjuvant comprising an alkyl methyl ester.

9. A method of preparing a composition according to any one of the preceding claims.

10. A method of controlling undesirable plant growth, the method comprising applying to the plants or the locus thereof a herbicidally effective amount of a composition according to any one of claims 1 to 8.

11. The method according to claim 10, wherein: The composition is applied to a rice field.

12. Use of xanthan gum for reducing the viscosity of an agrochemical composition, preferably wherein the agrochemical composition is an aqueous emulsion.

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