AU2009202360B2

AU2009202360B2 - Herbicidal composition

Info

Publication number: AU2009202360B2
Application number: AU2009202360A
Authority: AU
Inventors: Jessica Elizabeth Carty; Anthony Gerard Flynn; Philip Edward Pentland
Original assignee: Eureka Agresearch Pty Ltd
Current assignee: Eureka Agresearch Pty Ltd
Priority date: 2008-06-12
Filing date: 2009-06-12
Publication date: 2013-10-31
Anticipated expiration: 2029-06-12
Also published as: AU2009202360B8; AU2009202360A1

Abstract

The invention relates to high-loading liquid emulsifiable concentrate (EC) of trifluralin that is stable at 0 deg C and which comprises; i) at least 500 g/L (preferably at least 520g/L) of trifluralin; ii) 150 - 300 g/L of organic solvent for trifluralin having a flash point greater than about 60 deg C; iii) 120 - 300 g/L of organic ester liquid or liquids comprising methyl 10 ester functionality, and having a flash point of greater than about 60 deg C; and iv) 40 - 200 g/L of emulsifier.

Description

P/00/011 Regulation 3.2 AUSTRALIA Patents Act 1990 ORIGINAL COMPLETE SPECIFICATION STANDARD PATENT Invention Title: HERBICIDAL COMPOSITION Applicant: Eureka AgResearch Pty Ltd The following statement is a full description of this invention, including the best method of performing it known to me: I1 6067 JOL 2 HERBICIDAL COMPOSITION This invention relates to emulsifiable concentrates of trifluralin and to a method of preparing emulsifiable concentrates and a method of controlling weeds 5 using the emulsifiable concentrates. An emulsifiable concentrate (EC) formulation of a herbicide is a liquid formulation comprising herbicide, a water-insoluble solvent for the herbicide, and surfactant or surfactant blend. When added to water in a spray tank, the 10 emulsifiable concentrate forms an oil-in-water emulsion suitable for spray application. Emulsifiable concentrates are different from suspension concentrates in that the latter comprise an aqueous suspension of solid active ingredient (or solid vehicle bearing active ingredient) in water. Emulsifiable concentrates are also different from emulsion concentrates in that the latter 15 comprise a concentrated aqueous emulsion, rather than a readily emulsifiable oil phase. Commercially viable emulsifiable concentrates need to be efficacious, and also need to be stable in storage. Sufficient requirements for storage stability may 20 depend on the region of use - for example a trifluralin emulsifiable concentrate in Brazil need only be storage stable at 10 deg C or higher, since night-time temperatures in the key areas of use do not reach lower temperatures. By contrast, a trifluralin emulsion concentrate in Australia needs to be storage stable at 0 deg C. Stability tests are frequently carried out at the designated 25 temperature in the presence of seed crystals, over a period of two to seven days. A desirable characteristic for an emulsifiable concentrate is that it carries a high load of active ingredient. This characteristic is important for practical and 30 objective reasons which include reduced solvent utilisation and reduced packaging costs. High loads of active ingredient in a formulation are also more attractive to farmers. Trifluralin is soluble to a limited extent in aromatic organic solvents but 35 maximum possible loadings are reduced by a tendency of trifluralin to 3 precipitate at lower temperature. As a result most formulations of trifluralin are limited to about 480 grams per litre of emulsifiable concentrate. Also many of the solvents in which trifluralin is most soluble such as xylene are inflammable and present a potential risk on storage and handling. There is an ongoing need for improved emulsifiable concentrates that have high loadings of trifluralin. There is a particular need for high loading trifluralin emulsifiable concentrates that are increased in stability at low temperatures encountered in cooler climates. There is also a need for high loading trifluralin ) emulsifiable concentrates that are compatible with liquid fertiliser in a spray tank. The discussion of documents, acts, materials, devices, articles and the like is included in this specification solely for the purpose of providing a context for the present invention. It is not suggested or represented that any or all of these matters 5 formed part of the prior art base or were common general knowledge in the field relevant to the present invention as it existed before the priority date of each claim of this application. Summary ) This invention provides a high-loading liquid emulsifiable concentrate of trifluralin that is stable at 0 deg C and which comprises; i) at least 500 g/L (preferably at least 520g/L) of trifluralin; ii) 150 - 300 g/L of organic solvent selected from alkylbenzenes and having a flash point greater than about 60 C; 5 iii) 120 - 300 g/L of organic ester liquid selected from dimethyl esters of dicarboxylic acids, and having a flash point of greater than about 60 deg C; and iv) 40 - 200 g/L of emulsifier. In a further embodiment the invention provides a method of pre-emergent control of 0 weeds and in particular broadleaf and grass weeds comprising applying to soil a composition prepared by dilution of an emulsifiable concentrate (EC) comprising: i) at least 500 g/L (preferably at least 520g/L) of trifluralin; ii) 150 - 300 g/L of organic solvent selected from alkylbenzenes and having a flash 5 point greater than about 60 deg C; iii) 120 - 300 g/L of organic ester liquid selected from dimethyl esters of dicarboxylic acids and having a flash point of greater than about 60 deg C; and 4 iv) 40 - 200 g/L of emulsifier. The dilute composition may be prepared in a spray tank or using other equipment known in the art for dilution of herbicidal concentrates with water. The step of 5 diluting the composition may involve the addition of other herbicides or adjuvants of type known in the art. In a preferred embodiment the composition is combined with a liquid fertiliser such as urea ammonium nitrate or other nitrogenous liquid fertiliser. In a further embodiment the invention comprises a dilute trifluralin composition for ) application to soil wherein the dilute trifluralin composition has been prepared from an emulsifiable concentrate comprising: i) at least 500 g/L (preferably at least 520g/L) of trifluralin; ii) 150 - 300 g/L of organic solvent selected from alkylbenzenes and having a flash point greater than about 60 deg C; 5 iii) 120 - 300 g/L of organic ester liquid selected from dimethyl esters of dicarboxylic acids, and having a flash point of greater than about 60 deg C; and iv) 40 - 200 g/L of emulsifier. The dilute composition may further contain adjuvants or other herbicidal actives ) compatible with the diluted composition. In one preferred embodiment the diluted composition further comprises a nitrogenous fertiliser such as urea ammonium nitrate which may be added as a liquid fertiliser. Throughout the description and the claims of this specification the word comprise" 5 and variations of the word, such as "comprising" and "comprises" is not intended to exclude other additives, components, integers or steps. Detailed Description We have found that the presence of the dimethyl esters of dicarboxylic acids allows 0 a stable formulation of higher loading of trifluralin than has previously been available. The organic liquid ester comprises at least one selected from dimethyl esters of dicarboxylic acids and more preferably at least one selected from the group of 5 dimethyl succinate and dimethyl glutarate.

5 In a more preferred embodiment the organic ester liquid comprises succinate and dimethyl glutarate and most preferably the total ester liquid component comprises 50 - 85% dimethyl glutarate and 10 - 35% dimethyl succinate based on the total weight of organic liquid with methyl ester functionality. 5 In another embodiment at least 50 and more preferably at least 65% by weight of the ester solvent is dimethyl glutarate. The emulsifiable concentrate composition of the invention comprises at least 500g/L 3 (preferably 520g/L, more preferably 550g/L) of trifluralin. Most preferably the EC composition comprises at least 570 g/L of trifluralin. The upper end of the possible concentration range will depend on the specific formulation which is used but is typically no more than 650g/L (such as no more than 620g/L or no more than 600g/L) of trifluralin. 5 In one embodiment the formulation of the invention is storage stable at 0*C over a period of 7 days. Preferably the formulation does not deposit additional crystals when in contact with seed crystals over a period of 24 hrs at 00C, preferably over a period of 48 hrs, more preferably over a period of one week. The standard test for ) determining the low temperature stability of liquid formulations is CIPAC MT39.3 (1999). In one embodiment, the organic solvent for trifluralin comprises alkylbenzene moieties for example C8 to C16 (preferably C9 - C1o) di- and tri- alkylbenzenes such 5 as the product designated "Solvesso 150" which is sold by Exxon Mobil. The organic solvent will be selected to provide a flash point greater than about 60*C. The solvent preferably contains less than 5% by weight of the organic solvent of organics having a flash point of less than 600C such as xylene. 0 The EC composition of the invention comprises 40 - 200 g/L of emulsifier which enables emulsion formation to occur readily when the high-loading liquid emulsifiable concentrate comprising trifluralin is diluted in water or aqueous liquor, (for example, in a spray tank) for application in control of weeds. 5 The suitable emulsifier and specific concentration may be determined by a skilled chemist having regard to the objectives described herein. In a preferred embodiment the emulsifier component of the EC composition comprises an anionic emulsifier 6 component selected from the group consisting of alkylsulphonate or alkylaryl sulphonate anionic surfactant. The alkylsulphonate or alkylaryl sulphonate anionic surfactant material may 5 comprise dodecylbenzenesulphonic acid or a salt thereof particularly the calcium salt of dodecylbenzenesulphonic acid. Preferably this salt is dissolved in a solvent such as isobutanol, n-butanol, 2-ethylhexanol and Solvesso 100 (an alkyl benzene composition of boiling point initial 161 *C to dry point 171 *C). 3 The emulsifier component of the EC composition of the invention preferably includes a polyoxyalkylene non-ionic surfactant material such as a butyl polyoxyalkylene ether, preferably nonionic surfactants such as ethoxylated and/or propoxylated di- or tri-styrylphenols, ethoxylated and/or propoxylated fatty alcohols, ethoxylated and/or propoxylated fatty amines, ethoxylated and/or propoxylated alkylphenols such as 5 ethoxylated nonylphenols, block copolymers having polypropylene glycol blocks and polyethylene glycol blocks, sorbitan esters, ethoxylated oleic acids, ethoxylates castor oils, and mixtures thereof. In one embodiment the surfactant material includes alkyl sulphonate or 5 alkylaryl sulphonate anionic surfactant material and also includes polyoxyalkylene non-ionic surfactant material. The emulsifier material may alternatively or in addition comprise a long chain aliphatic amine ethoxylate such as tallow amine ethoxylate, preferably the 10 average number of ethoxy units is from 10 to 20 and more preferably from 14 to 16. In the more preferred embodiments of the invention the tallow amine ethoxylate comprises 3 - 10% by weight of the total weight of the emulsifier 15 component of the EC composition and still more, preferably 4 - 8% by weight of the emulsifier component. In another aspect, the high-loading trifluralin emulsifiable concentrate (EC) is used with a liquid nitrogen fertiliser. The EC may be added to the water in a 20 spray tank before, during or after the addition of fertiliser to the spray tank. The liquid nitrogen fertiliser may be any suitable fertiliser such as urea ammonium nitrate (UAN), or urea ammonium sulphate (UAS). (e.g. add EC to liquid fertiliser concentrate and then add this single pack to the water of the spray tank). 25 In one aspect sufficient EC is added to provide a concentration of 0.5% to 2.2% trifluralin in the spray tank. The concentration of liquid nitrogenous fertiliser may vary from 37.5% to 75%. 30 The invention will now be described with reference to the following examples. It is to be understood that the examples are provided by way of illustration of the invention and that they are in no way limiting to the scope of the invention.

Examples In the Examples the following components and nomenclature will be used: 5 TT - trifluralin technical (97% active) SFX - butylpolyoxyalkalene ether CAS:9038-95-3 such as is sold by Huntsman Corp. in the product "Termul" 5429. NSA - 70% solution calcium dodecylbenzene sulfonic acid in 2-ethylhexanol. TWT - tallow amine polyethoxylate (15) 10 JFF - blend of 22 parts dimethylsuccinate and 72 parts dimethylglutarate. SE - "Solvesso" 150 [surfactant] = [SFX + NSA + TWT] cs - cold stable at 0*C (CIPAC method MT39.3) ncs - not cold stable. 15 es - emulsion stable at room temperature with respect to phase separation. nes - emulsion not stable at room temperature Example 1 The composition of Example 1 shown in the table below was prepared by 20 mixing the components in the amounts by weight shown. Example 1 [trifluralin] = 525g/1 [surfactant] = 50g__/ T T 13.53 13.53 13.53 13.53 SFX 0.52 0.52 0.52 0.52 NSA 0.66 0.66 0.66 0.66 TWT 0.07 0.07 0.07 0.07 JFF 4.38 5.00 5.43 6.00 SE 7.34 6.97 6.79 6.47 S.G. (g/ml) 1.06 1.07 1.08 1.09 Cold Stability Cs Cs CS CS Emulsion Stability nes nes nes nes Example 2's 25 The composition of example 2 shown in the table below was prepared by mixing the components in the amounts by weight shown.

9 Example 2 [trifluralin] = 525g/I [surfactant] = 70g/l TT 13.53 13.53 13.53 13.53 SFX 0.72 0.72 0.72 0.72 NSA 0.94 0.94 0.94 0.94 TWT 0.09 0.09 0.09 0.09 JFF 4.38 5.00 5.43 6.00 SE 6.84 6.79 6.79 6.34 S.G. (g/ml) 1.06 1.08 1.10 1.11 Cold stability Cs CS CS CS Emulsion Stability es es nes nes Example 3 The composition of Example 3 shown in the table below was prepared by 5 mixing the components in the amounts by weight shown. Example 3 [trifluralin] = 525g/l [surfactant) = 90g/_ TT 13.53 13.53 13.53 13.53 SFX 0.93 0.93 0.93 0.93 NSA 1.20 1.20 1.20 1.20 TWT 0.12 0.12 0.12 0.12 JFF 4.38 5.00 5.43 6.00 SE 7.19 6.55 6.00 5.60 S.G. (g/ml) 1.09 1.09 1.09 1.10 Cold stability cs cs cs cs Emulsion Stability es es es es Example 4 The composition of Example 4 shown in the table below was prepared by 10 mixing the components in the amounts by weight shown. Example 4 [trifluralin] = 525g11 [surfactant] = 99.6g/l TT 13.53 13.53 13.53 13.53 SFX 1.03 1.03 1.03 1.03 NSA 1.33 1.33 1.33 1.33 TWT 0.13 0.13 0.13 0.13 JFF 4.38 5.00 5.43 6.00 SE 7.05 6.62 6.07 5.54 S.G. (g/ml) 1.10 1.10 1.10 1.10 Cold stability CS CS CS CS Emulsion Stability es es J es es 10 Example 5 The composition of Example 5 shown in the table below was prepared by mixing the components in the amounts by weight shown. Example 5 [trifluralin] = 525g/1 (surfactant] = 120g/l TT 13.53 13.53 13.53 13.53 SFX 1.24 1.24 1.24 1.24 NSA 1.60 1.60 1.60 1.60 TWT 0.16 0.16 0.16 0.16 JFF 4.38 5.00 5.43 6.00 SE 6.49 6.22 5.68 5.14 S.G. (g/ml) 1.10 1.11 1.11 1.11 Cold Stability CS CS CS CS Emulsion Stability es es es es 5 Example 6 The composition of Example 6 shown in the table below was prepared by mixing the components in the amounts by weight shown. Example 6 [trifluralin] = 550g/l [surfactant] = 50g/l TT 14.17 14.17 14.17 14.17 SFX 0.52 0.52 0.52 0.52 NSA 0.66 0.66 0.66 0.66 TWT 0.07 0.07 0.07 0.07 JFF 4.38 5.00 5.43 6.00 SE 7.52 6.99 6.57 6.13 S.G. (giml) 1.09 1.10 1.10 1.10 Cold Stability CS CS CS CS Emulsion Stability nes nes nes nes Example 7 10 The composition of Example 7 shown in the table below was prepared by mixing the components in the amounts by weight shown. Example 7 [trifluralin] = 550g/l [surfactant) = 70g/l TT 14.17 14.17 14.17 14.17 SFX 0.72 0.72 0.72 0.72 NSA 0.94 0.94 0.94 0.94 TWT 0.09 0.09 0.09 0.09 JFF 4.38 5.00 5.43 6.00 SE 6.89 6.61 6.05 5.70 S.G. (g/ml) 1.09 1.1 1.10 1.10 Cold Stability CS CS - Cs CS Emulsion Stability es es es es 11 Example 8 The composition of Example 8 shown in the table below was prepared by mixing the components in the amounts by weight shown. 5 Example 8 [trifluralin) = 550g/l [surfactant] = 909/1 TT 14.17 14.17 14.17 14.17 SFX 0.93 0.93 0.93 0.93 NSA 1.20 1.20 1.20 1.20 TWT 0.12 0.12 0.12 0.12 JFF 4.38 5.00 5.43 6.00 SE 6.39 6.18 5.63 5.12 S.G. (g/ml) 1.09 1.10 1.10 1.10 Cold Stability CS CS CS Cs Emulsion Stability es es es es Example 9 The composition of Example 9 shown in the table below was prepared by 10 mixing the components in the amounts by weight shown. Example 9 [trifluralin] = 550g11 [surfactant] = 99.6g/l TT 14.17 14.17 14.17 14.17 SFX 1.03 1.03 1.03 1.03 NSA 1.33 1.33 1.33 1.33 TWT 0.13 0.13 0.13 0.13 JFF 4.38 5.00 5.43 6.00 SE 6.03 5.7 5.28 4.69 S.G. (g/ml) 1.09 1.09 1.09 1.09 Cold Stability cs cs cs cs Emulsion Stability es es es es Example 10 15 The composition of Example 10 shown in the table below was prepared by mixing the components in the amounts by weight shown. 20 12 Example 10 [trifluralin] = 5509/l [surfactant] =120/L TT 14.17 14.17 14.17 14.17 SFX 1.24 1.24 1.24 1.24 NSA 1.60 1.60 1.60 1.60 TWT 0.16 0.16 0.16 0.16 JFF 4.38 5.00 5.43 6.00 SE 5.88 5.42 5.05 . 4.50 S.G. (g/ml) 1.10 1.10 1.11 1.11 Cold Stability ncs ncs ncs ncs Emulsion Stability es es es es Example 11 The composition of Example 11 shown in the table below was prepared by mixing the components in the amounts by weight shown. 5 Example 11 [trifluralin] = 5769/I [surfactant] = 50g/_ TT 14.85 14.85 14.85 14.85 SFX 0.52 0.52 0.52 0.52 NSA 0.66 0.66 0.66 0.66 TWT 0.07 0.07 0.07 0.07 JFF 4.38 5.00 5.43 6.00 SE 6.89 6.39 5.88 5.44 S.G. (g/ml) 1.09 1.10 1.10 1.10 Cold Stability CS CS CS CS Emulsion Stability nes nes nes nes Example 12 The composition of Example 12 shown in the table below was prepared by mixing the components in the amounts by weight shown. 10 Example 12 [trifluralin] = 576g/l [surfactant] = 70g/l TT 14.85 14.85 14.85 14.85 SFX 0.72 0.72 0.72 0.72 NSA 0.94 0.94 0.94 0.94 TWT 0.09 0.09 0.09 0.09 JFF 4.38 5.00 5.43 6.00 SE 6.25 5.93 5.43 5.17 S.G. (g/ml) 1.09 1.10 1.10 1.11 Cold Stability cs CS CS CS Emulsion Stability nes nes nes nes 13 Example 13 The composition of Example 13 shown in the table below was prepared by mixing the components in the amounts by weight shown. Example 13 [trifluralin] = 576g/Il [surfactant] = 90g/1 TT 14.85 14.85 14.85 14.85 SFX 0.93 0.93 0.93 0.93 NSA 1.20 1.20 1.20 1.20 TWT 0.12 0.12 0.12 0.12 JFF 4.38 5.00 5.43 6.00 SE 5.87 5.38 5.20 4.53 S.G.(g/ml) 1.09 1.10 1.11 1.10 Cold Stability ncs Cs cs cs Emulsion Stability es es es es 5 Example 14 The composition of Example 14 shown in the table below was prepared by mixing the components in the amounts by weight shown. Example 14 [trifluralin] = 576g/l [surfactant] = 99.6g/l TT 14.85 14.85 14.85 14.85 SFX 1.03 1.03 1.03 1.03 NSA 1.33 1.33 1.33 1.33 TWT 0.13 0.13 0.13 0.13 JFF 4.38 5.00 5.43 6.00 SE 5.85 5.18 4.94 4.73 S.G.(g/ml) 1.10 1.10 1.11 1.12 Cold Stability ncs ncs cs cs Emulsion Stability es es es es Example 15 10 The composition of Example 15 shown in the table below was prepared by mixing the components in the amounts by weight shown. Example 15 [trifluralin] = 576g/l [surfactant] = 120g/l Trifluralin Tech (97%) 14.85 14.85 14.85 14.85 Surfonix L429x 1.24 1.24 1.24 1.24 Nansa EVM 70/2E 1.60 1.60 1.60 1.60 Terwet 3780 0.16 0.16 0.16 0.16 Jeffsol AG171G 4.38 5.00 5.43 6.00 Solvesso 150 5.59 4.97 4.55 4.06 S.G. (g/ml) 1.11 1.11 1.11 1.12 Cold Stability ncs ncs ncs ncs Emulsion Stability es es es es 14 Example 16 The composition of Example 16 shown in the table below was prepared by mixing the components in the amounts by weight shown. 5 Example 16 [trifluralin] = 590g/l [surfactant] = 50g/l TT 15.21 15.21 15.21 15.21 SFX 0.52 0.52 0.52 0.52 NSA 0.66 0.66 0.66 0.66 TWT 0.07 0.07 0.07 0.07 JFF 4.38 5.00 5.43 6.00 SE 6.25 5.91 5.64 5.34 S.G. (g/ml) 1.08 1.09 1.10 1.11 Cold Stability ncs cs cs cs Emulsion Stability nes nes nes nes Example 17 The composition of Example 17 shown in the table below was prepared by 10 mixing the components in the amounts by weight shown. Example 17 [trifluralin] = 590g11 [surfactant] = 70g/1 TT 15.21 15.21 15.21 15.21 SFX 0.72 0.72 0.72 0.72 NSA 0.94 0.94 0.94 0.94 TWT 0.09 0.09 0.09 0.09 JFF 4.38 5.00 5.43 6.00 SE 5.97 5.66 5.35 4.8 S.G. (g/ml) 1.09 1.10 1.11 1.11 Cold Stability cs cs cs cs Emulsion Stability es es nes nes Example 18 15 The composition of Example 18 shown in the table below was prepared by mixing the components in the amounts by weight shown. 20 15 Example 18 [trifluralin] = 5909/1 [surfactant] = 90g11 TT 15.21 15.21 15.21 15.21 SFX 0.93 0.93 0.93 0.93 NSA 1.20 1.20 1.20 1.20 TWT 0.12 0.12 0.12 0.12 JFF 4.38 5.00 5.43 6.00 SE 5.62 5.15 4.79 4.30 S.G.(g/ml) 1.10 1.10 1.11 1.11 Cold Stability Cs Cs Cs ncs Emulsion Stability es es es nes Example 19 The composition of Example 19 shown in the table below was prepared by mixing the components in the amounts by weight shown. 5 Example 19 [trifluralin] = 5909/1 [surfactant] = 99.6g11 TT 15.21 15.21 15.21 15.21 SFX 1.03 1.03 1.03 1.03 NSA 1.33 1.33 1.33 1.33 TWT 0.13 0.13 0.13 0.13 JFF 4.38 5.00 5.43 6.00 SE 5.42 4.98 4.71 4.21 S.G.(g/ml) 1.10 1.11 1.11 1.12 Cold Stability ncs Cs ncs CS Emulsion Stability es es es nes Example 20 The composition of Example 20 shown in the table below was prepared by mixing the components in the amounts by weight shown. 10 Example 20 [trifluralin] = 590g11 [surfactant] 120g/l TT 15.21 15.21 15.21 15.21 SFX 1.24 1.24 1.24 1.24 NSA 1.60 1.60 1.60 1.60 TWT 0.16 0.16 0.16 0.16 JFF 4.38 5.00 5.43 6.00 SE 5.11 4.80 4.52 4.10 S.G. (g/ml) 1.11 1.12 1.13 1.13 Cold Stability cs Cs ncs Cs Emulsion Stability nes nes nes es 16 Example 21 The composition of Example 21 shown in the table below was prepared by mixing the components in the amounts by weight shown. Example 21 [trifluralin] = 600g/l [surfactant] 50g/I TT 15.46 15.46 15.46 15.46 SFX 0.52 0.52 0.52 0.52 NSA 0.66 0.66 0.66 0.66 TWT 0.07 0.07 0.07 0.07 JFF 4.38 5.00 5.43 6.00 SE 6.42 5.68 5.38 5.01 S.G. (gimi) 1.10 1.10 1.10 1.11 Cold Stability ncs ncs ncs ncs Emulsion Stability es nes nes nes 5 Example 22 The composition of Example 22 shown in the table below was prepared by mixing the components in the amounts by weight shown. Example 22 [trifluralin] = 600g/l [surfactant] = 70g/1 TT 15.46 15.46 15.46 15.46 SFX 0.72 0.72 0.72 0.72 NSA 0.94 0.94 0.94 0.94 TWT 0.09 0.09 0.09 0.09 JFF 4.38 5.00 5.43 6.00 SE 6.13 5.63 5.11 4.83 S.G. (g/ml) 1.11 1.11 1.11 1.12 Cold Stability ncs ncs ncs ncs Emulsion Stability nes nes es nes Example 23 10 The composition of Example 23 shown in the table below was prepared by mixing the components in the amounts by weight shown. Example 23 [trifluralin] = 600g/1 [surfactant] = 909/1 TT 15.46 15.46 15.46 15.46 SFX 0.93 0.93 0.93 0.93 NSA 1.20 1.20 1.20 1.20 TWT 0.12 0.12 0.12 0.12 JFF 4.38 5.00 5.43 6.00 SE 5.66 4.97 4.87 4.18 S.G. (g/ml) 1-.11 1.11 1.12 1.12 Cold Stability ncs ncs ncs ncs Emulsion Stability es nes nes nes 17 Example 24 The composition of Example 24 shown in the table below was prepared by mixing the components in the amounts by weight shown. Example 24 [triffuralin]= 600g/l surfactants =_.6a/ _ TT 15.46 15.46 15.46 15.46 SFX 1.03 1.03 1.03 1.03 NSA 1.33 1.33 1.33 1.33 TWT 0.13 0.13 0.13 0.13 JFF 4.38 5.00 5.43 6.00 SE 5.33 5.09 4.69 4.21 S.G. (g/m)1 1.12 1.11 1.13 | Cold Stability ncs ncs ncs ncs fusion Stability es es nes nes Example 25 The composition of Example 25 shown in the table below was prepared by mixing the components in the amounts by weight shown. Example 25 [trifluralin = 60011 [surfactant] 120/ _ TT 15.46 15.46 15.46 15.46 SFX 1.24 1.24 1.24 1.24_ NSA 1.60 1.60 1.60 1.60 TWT 0.16 0.16 0.16 0.16 j JFF 4.38 5.00 5.43 6.00 SE 5,24 4.45 4.14 3.78 S.G. (g/ml) 1.12 1.12 1.12 1.13 Cold Stabilityncs ncs ncs 0 Emulsion Stability es nes nes nes Finally, it is understood that various other modifications and/or alterations may be made without departing from the spirit of the present invention as outlined herein. 5

Claims

1. A high-loading liquid emulsifiable concentrate (EC) of trifluralin that is stable 5 at 0 deg C and which comprises; i) at least 500 g/L (preferably at least 520g/L) of.trifluralin; ii) 150 - 300 g/L of organic solvent selected from alkylbenzenes and having a flash point greater than about 60 deg C; iii) 120 - 300 g/L of organic ester liquid selected from dimethyl esters of a D dicarboxylic acids and having a flash point of greater than about 60 deg C; and iv) 40 - 200 g/L of emulsifier.

2. A high load EC of trifluralin according to claim 1, wherein the organic ester liquid 5 comprises at least one selected from the group of dimethyl succinate and dimethyl glutarate.

3. A high load EC of trifluralin according to claim 1 or claim 2, wherein the organic ester liquid comprises dimethyl succinate and dimethyl glutarate.

4. A high load EC of trifluralin according to any one of the previous claims comprising dimethyl succinate in the range 10 - 35% by weight, based on the total weight of organic ester.

5 5. A high load EC of trifluralin according to any one of the previous claims wherein the organic ester liquid comprises 60 - 85% by weight of the total organic ester of dimethyl glutarate and 10 - 35% by weight of the total organic ester of dimethyl succinate. 0

6. A high load EC of trifluralin according to any one of the previous claims wherein at least 50% and more preferably at least 65% by weight of the organic ester liquid is dimethyl glutarate.

7. A high load EC of trifluralin according to any one of the previous claims comprising 10 - 35% dimethyl succinate based on the total weight of organic 5 liquid with methyl ester functionality. 19

8. A high load EC of trifluralin according to any one of the previous claims wherein the emulsifier includes alkyl sulphonate or alkylaryl sulphonate anionic surfactant material. 5

9. A high load EC of trifluralin according to any one of the previous claims wherein the emulsifier component of the EC composition comprises a polyoxyalkylene non-ionic emulsifier.

10. A high load EC of trifluralin according to claim any one of the previous claims 0 wherein the emulsifier material comprises a long chain aliphatic amine ethoxylate such as tallow amine ethoxylate.

11. A high load EC of trifluralin according to claim any one of the previous claims wherein tallow amine ethoxylate constitutes in the range of from 3 - 10% by 5 weight of the total weight of the emulsifier component of the EC composition.

12. A high load EC of trifluralin according to any one of the previous claims wherein the trifluralin is present in an amount of at least 520g/L. of EC composition. J

13. A high load EC of trifluralin according to any one of the previous claims wherein the trifluralin is present in an amount of at least 550g/L of EC composition.

14. A high load EC of trifluralin according to any one of the previous claims wherein the EC composition is storage stable at 0 deg C over a period of 7 days. 5

15. A high load EC of trifluralin according to any one of the previous claims wherein the organic solvent comprises one or more C 8 to C 1 6 di- and tri-alkylbenzenes.

16. A high load EC of trifluralin according to any one of the previous claims wherein 0 the organic solvent comprises C 9 -C 1 o di- and tri-alkylbenzenes.

17. A method of controlling weeds and in particular broadleaf and grass weeds comprising applying to soil a composition prepared by dilution of an emulsifiable concentrate (EC) comprising: 5 i) at least 500 g/L (preferably at least 520g/L) of trifluralin; ii) 150 - 300 g/L of organic solvent selected from alkylbenzenes and having a flash point greater than about 60 deg C; 20 iii) 120 - 300 g/L of organic liquid selected from dimethyl esters of dicarboxylic acids and having a flash point of greater than about 60 deg C; and iv) 40 - 200 g/L of emulsifier. 5

18. A method of controlling weeds and in particular broadleaf and grass weeds according to claim 17 wherein the EC composition is combined with a liquid fertiliser such as urea ammonium nitrate or other nitrogenous liquid fertiliser.

19. A dilute trifluralin composition for application to soil wherein the dilute trifluralin 0 composition has been prepared from an emulsifiable concentrate comprising: i) at least 500 g/L (preferably at least 520g/L) of trifluralin; ii) 150 - 300 g/L of organic solvent selected from alkylbenzenes and having a flash point greater than about 60 deg C; iii) 120 - 300 g/L of organic ester liquid selected from dimethyl esters of 5 dicarboxylic acids and having a flash point of greater than about 60 deg C; and iv) 40 - 200 g/L of emulsifier.

20. A dilute trifluralin composition according to claim 19 further comprising a 0 nitrogenous fertiliser,