HIGH-LOAD SOLUTION CONCENTRATES OF DICAMBA

Abstract

The invention relates to an agrochemical composition comprising the potassium salt of dicamba and an adjuvant selected from a) a polyalkylene oxide block-copolymer, b) a hyperbranched polycarbonate, and c) a solvent selected from C.sub.1-C.sub.6-alkyl lactate, C.sub.3-C.sub.6-lactone and N—C.sub.1-C.sub.15-alkyl pyrrolidone. It also relates to a method of controlling undesired vegetation, and/or for regulating the growth of plants, wherein the agrochemical composition is allowed to act on the respective pests, their environment, or the crop plants to be protected from the respective pest, on the soil and/or on the crop plants and/or on their environment; to a method for producing the agrochemical composition; to an adjuvant composition for increasing the solubility of the potassium salt of dicamba in an aqueous composition comprising a mixture of additive a) or additive b) with additive c) fine droplet formation.

Claims

1. An aqueous agrochemical composition comprising the potassium salt of dicamba, and an additive selected from the group consisting of a) a polyalkylene oxide block-copolymer of formula (I)
R.sup.1O(EO).sub.n(PO).sub.m(EO).sub.pR.sup.2  (I), wherein EO is CH.sub.2CH.sub.2O; PO is CH.sub.2CH(CH.sub.3)O; R.sup.1, R.sup.2 are H, or C.sub.1-C.sub.3-alkyl; n, p are independently a natural number from 10 to 250, preferably 20 to 200; and m is a natural number from 10 to 100, preferably 20 to 70; b) a hyperbranched polycarbonate, which is connected to a linear polymer comprising polyethylene oxide; and c) a solvent selected from C.sub.1-C.sub.6-alkyl lactate, C.sub.3-C.sub.6-lactone and N—C.sub.1-C.sub.15-alkyl pyrrolidone.

2. The agrochemical composition according to claim 1 comprising additive a), wherein the ratio of (n+p)/m in formula I is 1:1 to 10:1.

3. The agrochemical composition according to claim 1 comprising additive b), wherein the hyperbranched polycarbonate is connected to a polyethyleneglycol-mono-C.sub.1-C.sub.18-alkylether.

4. The agrochemical composition according to claim 1 comprising additive b), wherein the hyperbranched polycarbonate contains a polyetherol based on an alcohol with at least 3 OH groups and 1 to 30 molecules alkylene oxide.

5. The agrochemical composition according to claim 1 comprising glyphosate and/or glufosinate and/or pyroxasulfone.

6. The agrochemical composition according to claim 1, wherein the potassium salt of dicamba is present in an amount of at least 55 wt % based on the total weight of the agrochemical composition.

7. The agrochemical composition according to claim 1 containing mixture of additive a) or additive b), and additive c).

8. The agrochemical composition according to claim 1 containing at least 22 wt % of water based on the total weight of the formulation.

9. The agrochemical composition according to claim 1, wherein a concentration of a sum of all additives a), b), and c), is from 1 to 35 wt % based on the total weight of the agrochemical composition.

10. The agrochemical composition according to claim 1 containing a side product of dicamba-K selected from the group consisting of 3,5-dichloro-2-methoxybenzoic acid, 3,6-dichloro-2-hydroxybenzoic acid, 3,5-dichloro-2-hydroxybenzoic acid, 3-chloro-2,6-dimethoxybenzoic acid, 3,4-dichloro-2-methoxybenzoic acid, 3,4-dichloro-2-hydroxybenzoic acid, and/or 3,5-dichloro-4-methoxybenzoic acid, and a potassium salt of any of them.

11. The agrochemical composition according to claim 10, wherein the concentration of the side product is at least 1 wt % based on the total weight of the agrochemical composition.

12. A method for producing the agrochemical composition as defined in claim 1 comprising the step of contacting dicamba-K with the additive as defined in claim 1.

13. A method of controlling undesired vegetation, and/or for regulating the growth of plants, wherein the agrochemical composition, as defined in claim 1, is allowed to act on the respective pests, their environment, or the crop plants to be protected from the respective pest, on the soil and/or on the crop plants and/or on their environment.

14. An adjuvant composition for increasing the solubility of dicamba-K in an aqueous composition, comprising a mixture of the additive a) or the additive b) and additive c) as defined in claim 1.

15. A method for reducing the spray drift of an aqueous composition comprising the potassium salt of dicamba, comprising the step of contacting the potassium salt of dicamba with additive a), b), or c) as defined in claim 1, and water.

Description

EXAMPLES

[0211] The following ingredients were used for preparing the agrochemical compositions of the examples.

[0212] Dicamba-K-A: potassium salt of dicamba, 95.3% purity.

[0213] Dicamba-K-B: potassium salt of dicamba, 99.9% purity Dicamba-K-C: potassium salt of dicamba, 93.0% purity

[0214] Side products of dicamba material: 3,5-dichloro-2-methoxybenzoic acid, 3,6-dichloro-2-hydroxybenzoic acid, 3,5-dichloro-2-hydroxybenzoic acid, 3-chloro-2,6-dimethoxybenzoic acid, 3,4-dichloro-2-methoxybenzoic acid, 3,4-dichloro-2-hydroxybenzoic acid, 3,5-dichloro-4-methoxybenzoic acid and their potassium salts.

[0215] Dicamba-SL: 600 g/l solution of N,N-Bis-(3-aminopropyl)methylammonium salt of dicamba in water.

[0216] Polymer A: polyalkylene oxide block-copolymer of formula (I), wherein m is from 50 to 60, and n, p are independently from 45 to 55.

[0217] Polymer B: polyalkylene oxide block-copolymer of formula (I), wherein m is from 25 to 35, and n, p are independently from 70 to 80.

[0218] Polymer C: hyperbranched polycarbonate connected to methyl polyethylene glycol, prepared as described in Synthesis Example 5 of WO2010130599

[0219] Solvent A: n-propyl lactate

[0220] Solvent B: N-butyl pyrrolidone

[0221] Solvent C: N-octyl pyrrolidone

[0222] Solvent D: N-dodecyl pyrrolidone

[0223] Solvent E: gamma-butyrolactone

[0224] Adjuvant A: non-ionic adjuvant composition comprising dimethylpolysiloxane, alkanolamides, fatty acids, and alkyl aryl polyoxylkane ethers.

Example-1

[0225] A soluble concentrate of dicamba-K-A was produced (SL-1). For this purpose, the following compounds were added in a vessel in the order and amount given in Table A. The resulting mixture was then stirred until a clear and homogeneous liquid was obtained.

TABLE-US-00001 TABLE A components of SL-1 in [g] Compound Amount Dicamba-K-A 56.9 Demineralized H.sub.2O 46.75 Solvent B 6.68 Solvent E 6.68 Polymer A 6.68

Example 2

[0226] Soluble concentrates SL-2 to SL-10 were produced in analogy to Example-1. The amount of the ingredients is listed in Table B.

TABLE-US-00002 TABLE B components of SL-2 to SL-10 in [g]. Compound SL-2 SL-3 SL-4 SL-5 SL-6 SL-7 SL-8 SL-9 SL-10 Dicamba-K-A 56.66  56.66  56.66  56.66  56.66  56.66  56.66  56.66  56.66  H.sub.2O.sub.(demin.) 46.75  46.75  46.75  46.75  46.75  46.75  46.75  46.75  46.75  Solvent A — — 6.68 — — — — — — Solvent B — — — 6.68 — — 6.68 — — Solvent C 6.68 — — — 6.68 — — 6.68 — Solvent D — 6.68 — — — 6.68 — — 6.68 Solvent E 6.68 6.68 6.68 6.68 6.68 6.68 6.68 6.68 6.68 Polymer A 6.68 6.68 — — — — — — — Polymer B — — 6.68 6.68 6.68 6.68 — — — Polymer C — — — — — — 6.68 6.68 6.68

Example-3

[0227] All soluble concentrates SL-1 to SL-10 were analyzed after preparation by visual inspection. SL-1 to SL-14 formed clear solutions comprising dicamba-K-A.

Example-4

[0228] Comparative soluble concentrate SL-C.sub.1 was prepared by mixing 66 wt % water and 44 wt % of Dicamba-K-A. Dicamba-K-A contained the following side products in the experimentally determined concentrations and concentration ranges provided in brackets: 3,5-dichloro-2-methoxybenzoic acid (10 to 70 g/kg), 3,6-dichloro-2-hydroxybenzoic acid (5 to 30 g/kg), 3,5-dichloro-2-hydroxybenzoic acid (0.5 to 25 g/kg).

[0229] The mixture formed a turbid liquid, full of matters in suspension that did not dissolve in the water and sedimented upon storage.

Example-5

[0230] Fine Droplet Ratio properties of the diluted soluble concentrates SL-1 to SL-10 in admixture to glyphosate were analyzed. To this end, 1.22 L of a soluble concentrate selected from SL-1 to SL-14 was mixed with 2.07 L of a soluble concentrate comprising 540 g/l of the potassium salt of glyphosate (hereinafter “glyphosate-K”), which mixture was diluted with water to a total volume of 94 L. The resulting spray solution was then sprayed either with an AIXR nozzle (“TeeJet Flat Spray Tip”) or a TTI nozzle (“Turbo TeeJet Induction Flat Spray Tip”) at a pressure of 2.76 bar. The droplet size distribution was measured with a Sympatec Helos KF Laser diffraction device. Measurement was in 31 particle size classes from 18 to 3500 μm. Measurement was made at an angle of 0 at a distance of 30.5 cm from the nozzle. The analysis of data was based on 10 measurements collected in two runs. If necessary, the lenses were cleaned inbetween.

[0231] For comparison, a spray solution was prepared by mixing 0.93 L of an aqueous soluble concentrate containing 754 g/L dicamba N,N-bis-(3-aminopropyl)methylammonium (SL-C2) with 2.07 L of a soluble concentrate comprising 540 g/L of the potassium salt of glyphosate and diluted with water to a total volume of 94 L. Table D shows the fractions of fine droplets for the different nozzle types and the tested soluble concentrates SL-1 to SL-10 in comparison with SL-C2.

TABLE-US-00003 TABLE D measurement of fine droplets <100 μm of SL-1 to SL-10 and SL-C2 after admixture to glyphosate potassium salt and dilution with water Fine droplets Fine droplets with mean Soluble with mean diameter diameter below 100 μm concentrate below 100 μm by spraying by spraying with tested with AIXR nozzle in [%]. TTI nozzle in [%]. SL-1 7.6 1.23 SL-2 8.79 0.89 SL-3 6.87 1.18 SL-4 7.03 1.25 SL-5 8.49 1.19 SL-6 10.05 0.87 SL-7 7.71 0.62 SL-8 8.9 1.44 SL-9 9.53 0.97 SL-10 7.28 1.08 SL-C2 8.58 1.04

Example 6

[0232] Soluble concentrates SL-11 to SL-37 were produced in analogy to Example-1. The amount of the ingredients is listed in Tables E, F, G, and H.

TABLE-US-00004 TABLE E components of SL-11 to SL-18 in [g]. Compound SL-11 SL-12 SL-13 SL-14 SL-15 SL-16 SL-17 SL-18 Dicamba-K-A 736.1 736.1 736.1 736.1 736.1 736.1 736.1 736.1 H.sub.2O.sub.(demin.) 313.9 310.1 281.9 366.5 366.5 388.3 422.9 422.9 Solvent A 50.0 56.4 84.6 — 56.4 84.6 — 56.4 Polymer C 200.0 197.4 197.4 197.4 141.0 141.0 141.0 84.6

TABLE-US-00005 TABLE F components of SL-19 to SL-26 in [g]. Compound SL-19 SL-20 SL-21 SL-22 SL-23 SL-24 SL-25 SL-26 Dicamba-K-A 736.1 736.1 736.1 736.1 736.1 736.1 736.1 736.1 H.sub.2O.sub.(demin.) 394.7 479.3 338.3 394.7 451.1 310.1 281.9 253.7 Solvent A 84.6 — 28.2 28.2 28.2 28.2 56.4 84.6 Polymer C 84.6  84.6 197.4 141.0 84.6 225.6 225.6 225.6

TABLE-US-00006 TABLE G components of SL-27 to SL-34 in [g]. Compound SL-27 SL-28 SL-29 SL-30 SL-31 SL-32 SL-33 SL-34 Dicamba-K-A 736.1 736.1 736.1 736.1 736.1 736.1 736.1 736.1 H.sub.2O.sub.(demin.) 253.7 310.1 366.5 338.3 451.1 422.9 394.7 366.5 Solvent A 112.8 112.8 112.8 141.0 84.6 112.8 141.0 169.2 Polymer C 197.4 141.0 84.6 84.6 28.2 28.2 28.2 28.2

TABLE-US-00007 TABLE H components of SL-35 to SL-37 in [g]. Compound SL-35 SL-36 SL-37 Dicamba-K-A 736.1 736.1 736.1 H.sub.2O.sub.(demin.) 338.3 366.5 479.3 Solvent A 197.4 197.4 84.6 Polymer C 28.2 — —

Example 7

[0233] Soluble concentrates SL-12 to SL-37 were analyzed directly after preparation by visual inspection. The following soluble concentrates formed clear solutions: SL-12, SL-13, SL-14, SL-15, SL-16, SL-18, SL-19, SL-21, SL-22, SL-24, SL-28, SL-29, SL-30, SL-31, SL-31, SL-32, SL-33, SL-34, SL35, SL-36, SL-37.

[0234] The following soluble concentrates formed cloudy mixtures: SL-17, SL-23.

[0235] The following soluble concentrates formed turbid mixtures containing undissolved solid: SL-20, SL-25, SL-26, SL-27.

Example 8

[0236] Soluble concentrates SL-12 to SL-24 and SL-28 to SL-37 were incubated at 54° C. for four weeks and then analyzed by visual inspection. The following soluble concentrates formed clear solutions: SL-12, SL-13, SL-14, SL-15, SL-16, SL-18, SL-19, SL-20, SL-21, SL-22, SL-23, SL24, SL-28, SL-29, SL-30, SL-31, SL-31, SL-32, SL-33, SL-34, SL35, SL-36, SL-37.

Example 9

[0237] Soluble concentrates SL-12 to SL-24 and SL-28 to SL-37 were incubated at 0° C. for four weeks and then analyzed by visual inspection. The following soluble concentrates formed clear solutions: SL-12, SL-14, SL-15, SL-16, SL-18, SL-19, SL-21, SL-22, SL-28, SL-29, SL-30, SL-31, SL-32, SL-33, SL-34, SL-35, SL-36

[0238] The following soluble concentrates formed cloudy mixtures: SL-17

[0239] The following soluble concentrates formed crystals or precipitated solid: SL-13, SL-20, SL-23, SL-24, SL-37.

Example 10

[0240] Soluble concentrates SL-12 to SL-24 and SL-28 to SL-37 were incubated at 10° C. for four weeks and then analyzed by visual inspection. The following soluble concentrates formed clear solutions: SL-12, SL-14, SL-15, SL-16, SL-18, SL-19, SL-21, SL-22, SL-28, SL-29, SL-30, SL31, SL-32, SL-33, SL-34, SL-35, SL-36

[0241] The following soluble concentrates formed cloudy mixtures: SL-17

[0242] The following soluble concentrates formed crystals or precipitated solid: SL-13, SL-20, SL-23, SL-24, SL-37.

Example 11

[0243] Soluble concentrates SL-38 to SL-60 were produced in analogy to Example-1. The amount of the ingredients is listed in Tables J, K, and L.

TABLE-US-00008 TABLE J components of SL-38 to SL-45 in [g]. Compound SL-38 SL-39 SL-40 SL-41 SL-42 SL-43 SL-44 SL-45 Dicamba-K-A 736.1 736.1 736.1 736.1 736.1 736.1 736.1 736.1 H.sub.2O.sub.(demin.) 310.1 281.9 366.5 338.3 422.9 394.7 338.3 394.7 Solvent B 56.4 84.6 56.4 84.6 56.4 84.6 28.2 28.2 Polymer C 197.4 197.4 141.0 141.0 84.6 84.6 197.4 141.0

TABLE-US-00009 TABLE K components of SL-46 to SL-53 in [g]. Compound SL-46 SL-47 SL-48 SL-49 SL-50 SL-51 SL-52 SL-53 Dicamba-K-A 736.1 736.1 736.1 736.1 736.1 736.1 736.1 736.1 H.sub.2O.sub.(demin.) 451.1 310.1 281.9 253.7 253.7 310.1 366.5 338.3 Solvent B 28.2 28.2 56.4 84.6 112.8 112.8 112.8 141.0 Polymer C 84.6 225.6 225.6 225.6 197.4 141.0 84.6 84.6

TABLE-US-00010 TABLE L components of SL-54 to SL-60 in [g]. Compound SL-54 SL-55 SL-56 SL-57 SL-58 SL-59 SL-60 Dicamba-K-A 736.1 736.1 736.1 736.1 736.1 736.1 736.1 H.sub.2O.sub.(demin.) 451.1 422.9 394.7 366.5 338.3 366.5 479.3 Solvent B 84.6 112.8 141.0 169.2 197.4 197.4 84.6 Polymer C 28.2 28.2 28.2 28.2 28.2 — —

Example 12

[0244] Soluble concentrates SL-61 to SL-72 were produced in analogy to Example-1. The amount of the ingredients is listed in Tables M, and N.

TABLE-US-00011 TABLE M components of SL-61 to SL-68 in [g]. Compound SL-61 SL-62 SL-63 SL-64 SL-65 SL-66 SL-67 SL-68 Dicamba-K-A 736.1 736.1 736.1 736.1 736.1 736.1 736.1 736.1 H.sub.2O.sub.(demin.) 253.7 253.7 310.1 366.5 338.3 451.1 422.9 394.7 Solvent E 84.6 112.8 112.8 112.8 141.0 84.6 112.8 141.0 Polymer C 225.6 197.4 141.0 84.6 84.6 28.2 28.2 28.2

TABLE-US-00012 TABLE N components of SL-69 to SL-72 in [g]. Compound SL-69 SL-70 SL-71 SL-72 Dicamba-K-A 736.1 736.1 736.1 736.1 H.sub.2O.sub.(demin.) 366.5 338.3 366.5 479.3 Solvent E 169.2 197.4 197.4 84.6 Polymer C 28.2 28.2 — —

Example 13

[0245] Soluble concentrates SL-61 to SL-72 were analyzed directly after preparation by visual inspection. The following soluble concentrates formed clear solutions: SL-63, SL-64, SL-65, SL-66, SL-67, SL-68, SL-69, SL-70, SL-71.

[0246] The following soluble concentrates formed turbid mixtures containing undissolved solid: SL-61, SL-62, SL-72.

Example 14

[0247] Soluble concentrates SL-61 to SL-72 were analyzed after incubation for four weeks at 54° C. by visual inspection. The following soluble concentrates formed clear solutions: SL-63, SL-64, SL65, SL-66, SL-67, SL-68, SL-69, SL-70, SL-71.

[0248] The following soluble concentrates formed turbid mixtures containing undissolved solid: SL-61, SL-62, SL-72.

Example 15

[0249] The Fine Droplet Ratio properties of the diluted soluble concentrates SL-30 to SL-37 in admixture to glyphosate were analyzed. To this end, 0.94 L of a soluble concentrate selected from SL-1 to SL-14 was mixed with 2.07 L of a soluble concentrate comprising 540 g/l of the potassium salt of glyphosate, which mixture was diluted with water to a total volume of 94 L. The resulting spray solution was then sprayed either with an AIXR nozzle (“TeeJet Flat Spray Tip”) with a pressure of 2.76 bar or a TTI nozzle (“Turbo TeeJet Induction Flat Spray Tip”) at a pressure of 4.13 bar. The droplet size distribution was measured with a Sympatec Helos KF Laser diffraction device. Measurement was in 31 particle size classes from 18 to 3500 μm. Measurement was made at an angle of 0° at a distance of 30.5 cm from the nozzle. The analysis of data was based on 10 measurements collected in two runs. If necessary, the lenses were cleaned inbetween.

[0250] For comparison, a spray solution was prepared by mixing 0.93 L of an aqueous soluble concentrate containing 754 g/L dicamba N,N-bis-(3-aminopropyl)methylammonium (SL-C3) with 2.07 L of a soluble concentrate comprising 540 g/L of the potassium salt of glyphosate and diluted with water to a total volume of 94 L. Table P showed the fractions of fine droplets for the different nozzle types and the tested soluble concentrates SL-30 to SL-37 in comparison with SL-C.sub.3.

TABLE-US-00013 TABLE P measurement of fine droplets <100 μm of SL-30 to SL-37 and SL-C3 after admixture to glyphosate potassium salt and dilution with water Fine droplets with Fine droplets with Soluble mean diameter below mean diameter below concentrate 100 μm by spraying 100 μm by spraying with tested with AIXR nozzle in [%]. TTI nozzle in [%]. SL-30 8.35 3.55 SL-31 8.25 3.21 SL-32 7.96 3.24 SL-33 8.20 3.25 SL-34 8.02 3.26 SL-35 8.39 3.36 SL-36 8.28 3.35 SL-37 8.23 3.51 SL-C3 8.4 3.14

Example 16

[0251] Soluble concentrates SL-73 to SL-108 were produced in analogy to Example-1. The amount of the ingredients is listed in Tables Q, R, S, T, U, and V.

TABLE-US-00014 TABLE Q components and densities of SL-73 to SL-80. Compound SL-73 SL-74 SL-75 SL-76 SL-77 SL-78 SL-79 SL-80 Dicamba-K-A [g] 736.1 736.1 736.1 736.1 736.1 736.1 736.1 736.1 Solvent A [g] — 84.6 28.2 112.8 — — — — Solvent B [g] — — — — — — — — Solvent E [g] — — — — 84.6 84.6 112.8 169.2 Polymer B [g] — — — — — — — — Polymer C [g] 197.4 84.6 141 141 141 84.6 84.6 28.2 Water [g] 366.5 394.7 394.7 310.1 338.3 394.7 366.5 366.5 Density [g/ml] at 1.33 1.319 1.325 1.323 1.337 1.331 1.335 1.338 20° C.

TABLE-US-00015 TABLE R components of SL-81 to SL-85 in [g]. Compound SL-81 SL-82 SL-83 SL-84 SL-85 SL-86 SL-87 Dicamba-K-A [g] 736.1 — — — — — Dicamba-K-C [g] — 756.3 756.3 755.9 755.9 755.9 755.9 Solvent A [g]  56.4 16.92 56.4 84.6 112.8 — — Solvent B [g] — 50.76 112.8 — — — — Solvent E [g] — 16.92 — — —  84.6 84.6 Polymer B [g] — — — 84.6 141   141   84.6 Polymer C [g] 141.0 84.6 28.2 — — — — Water 366.5 389.5 361.27 375.2 290.6 318.8 375.2 Density [g/ml] at   1.321 1.315 1.315 1.332   1.338 N.A. 1.345 20° C.

TABLE-US-00016 TABLE S components of SL-86 to SL-92 in [g]. Compound SL-88 SL-89 SL-90 SL-91 SL-92 Dicamba-K-C [g] 755.9 755.9 755.9 756.3 756.3 Solvent A [g] — — — 16.92 56.4 Solvent B [g] — — 56.4 50.76 112.8 Solvent E [g] 112.8 169.2 — 16.92 — Polymer B [g] 84.6 28.2 141.0 84.6 28.2 Polymer C [g] — — — — — Water [g] 347.0 347.0 347.0 389.5 361.27 Density [g/ml] at 1.348 1.349 N.A. 1.314 1.328 20° C.

TABLE-US-00017 TABLE T components and densities of SL-93 to SL-100. Compound SL-93 SL-94 SL-95 SL-96 SL-97 SL-98 SL-99 SL-100 Dicamba-K-B [g] 755.6 755.6 755.6 755.6 755.6 755.6 755.6 755.6 Solvent A [g] — 84.6 28.2 112.8 — — — — Solvent B [g] — — — — — — — — Solvent E [g] — — — — 84.6 84.6 112.8 169.2 Polymer B [g] — — — — — — — — Polymer C [g] 197.4 84.6 141 141 141 84.6  84.6  28.2 Water [g] 366.5 394.7 394.7 310.1 338.3 394.7 366.5 366.5 Density [g/ml] at 1.34 1.3 1.3 1.331 1.346 1.342   1.345   1.348 20° C.

TABLE-US-00018 TABLE U components of SL-101 to SL-107 in [g]. Compound SL-101 SL-102 SL-103 SL-104 SL-105 SL-106 SL-107 Dicamba-K-B [g] 755.6 703 703 703 703 703 703 Solvent A [g] 56.4 16.92 56.4 84.6 112.8 — — Solvent B [g] — 50.76 112.8 — — — — Solvent E [g] — 16.92 — — —   84.6 84.6 Polymer B [g] — — — 84.6 141 141 84.6 Polymer C [g] 141.0 84.6 28.2 — — — — Water 366.5 389.5 361.27 375.2 290.6   318.8 375.2 Density [g/ml] at 1.331 1.305 1.305 1.282 1.312 N.A. 1.317 20° C.

TABLE-US-00019 TABLE V components of SL-108 to SL-112 in [g]. Compound SL-108 SL-109 SL-110 SL-111 SL-112 Dicamba-K-B [g] 703 703 703 703 703 Solvent A [g] — — — 16.92 56.4 Solvent B [g] — — 56.4 50.76 112.8 Solvent E [g] 112.8 169.2 — 16.92 — Polymer B [g] 84.6 28.2 141.0 84.6 28.2 Polymer C [g] — — — — — Water [g] 347.0 347.0 347.0 389.5 361.27 Density [g/ml] at 1.322 1.322 N.A. 1.305 1.294 20° C.

Example 17

[0252] An atomization study was conducted to measure Fine Droplet Ratios produced by spraying simulated spray tank mixtures through a Turbo Teejet Induction (TTI) 11004 nozzle at a pressure of 63 psi to simulate ground boom applications. Spray tank mixtures contained the soluble concentrates as indicated in Table W at a final concentration of 1 wt %, Adjuvant A at a final concentration of 0.25 wt %, and water. The spray droplet size spectra were measured using a laser diffraction particle size analyzer. Data were expressed as the entire droplet size spectra and compared using the spray volume contained in relatively small droplets with mean diameter between 2-105 um and 2-141 μm. A tank mix containing Dicamba-SL at a final concentration of 1 wt %, Adjuvant A at a final concentration of 0.25 wt % and water was used as a control (SL-C4).

TABLE-US-00020 TABLE W measurement of fine droplets of SL-73 to SL-81 and SL-C4 Soluble Fine droplets with mean Fine droplets with mean concentrate diameter between diameter between tested 2 and 105 μm in [%] 2 and 141 μm in [%] SL-73 0.39 0.86 SL-74 0.43 0.94 SL-75 0.43 0.92 SL-76 0.41 0.90 SL-77 0.52 1.06 SL-78 0.56 1.11 SL-79 0.57 1.13 SL-80 0.63 1.19 SL-81 0.40 0.88 SL-C4 0.42 0.88

Example 18

[0253] Soluble concentrates SL-78 to SL-108 were analyzed for their volatility in the presence of glyphosate-K. To this end, 0.94 L of a soluble concentrate selected from SL-78 to SL-108 was mixed with 2.07 L of a soluble concentrate comprising 540 g/l of the potassium salt of glyphosate, which mixture was diluted with water to a total volume of 94 L. Samples were further diluted with water to ensure similar amounts of active ingredients per area in the test tubes as obtained by spraying the active ingredients at the recommended application rates in the field. The samples were then incubated in glass tubes that were contained in water baths. The samples were incubated for 24 hours at 70° C. Volatilized sample material was constantly removed from the tubes by an air conduct. Residual amounts of dicamba are determined relative to the applied amount. The reported volatility is [1−(residual amount/applied amount)] in percent. The results were summarized in Tables X to AB below.

TABLE-US-00021 TABLE X Volatility measured in a Büchi Multivapor P-12 for samples SL-73 to SL-81 Soluble concentrate SL-73 SL-74 SL-75 SL-76 SL-77 SL-78 SL-79 SL-80 SL-81 Volatility [%] 5.0 5.3 6.2 5.7 3.9 5.3 6.0 5.9 6.1

TABLE-US-00022 TABLE Y Volatility measured in a Büchi Multivapor P-12 for samples SL-82 to SL-90. Soluble concentrate SL-82 SL-83 SL-84 SL-85 SL-86 SL-87 SL-88 SL-89 SL-90 Volatility [%] 16.0 10.6 10.6 10.7 n.m. 11.4 10.2 18.0 n.m. n.m. = not measured

TABLE-US-00023 TABLE Z Volatility measured in a Büchi Multivapor P-12 for samples SL-91 to SL-97 Soluble concentrate SL-91 SL-92 SL-93 SL-94 SL-95 SL-96 SL-97 Volatility [%] 13.7 11.3 10.4 4.1 9.9 5.8 5.3

TABLE-US-00024 TABLE AA Volatility measured in a Büchi Mutivapor P-12 for samples SL-98 to SL-104 Soluble concentrate SL-98 SL-99 SL-100 SL-101 SL-102 SL-103 SL-104 Volatility [%] 6.9 10.5 5.5 11.5 7.6 8.2 6.9

TABLE-US-00025 TABLE AB Volatility measured in a Büchi Multivapor P-12 for samples SL-105 to SL-112. Soluble concentrate SL-105 SL-106 SL-107 SL-108 SL-109 SL-110 SL-111 SL-112 Volatility [%] 6.3 n.m. 10.8 9.0 13.0 n.m. 10.9 14.5 n.m. = not measured.

Example 19

[0254] A quantitative Humi-Dome study was carried out. To this end, two treated glass plates were placed in a plastic tray, which was covered with a clear plastic Humi-Dome (overall size 25 cm wide×50 cm long×20 cm tall by Hummert International). The Humi-Dome was fitted with an air sampling filter cassette containing fiberglass and cotton pad filter media, which was connected to a vacuum pump with a flow rate of 2 liters per minute. Individual Humi-Domes representing different study treatments and replicates were placed in a controlled growth chamber environment of 35° C. and 25 to 40% humidity. Soluble concentrates SL-73 to SL-81 as well as comparative soluble concentrate SL-C5 containing a control Dicamba-SL were tested in tank-mixes with water and 0.25 vol-% of Adjuvant A. Treatments were applied to the glass plates using a laboratory track sprayer using a TeeJet 95015E nozzle by Spraying Systems and a 146 U/ha spray volume. The application rate of dicamba was 560 grams of acid equivalent per hectare. After 24 hours of air sampling, filters were collected, extracted and analyzed for dicamba content using gas-chromatography coupled mass spectrometry. The total amount of dicamba captured was then divided by total volume of the air flow through the filter to calculate the total amount dicamba captured/unit volume of air and the relative reduction of dicamba captured in the filter compared to SC-C.sub.5 as summarized in Table AC.

TABLE-US-00026 TABLE AD reduction of dicamba captured in filter compared with the control as measured in Humi-Dome assay [%]. Reduction of dicamba captured in Soluble concentrate filter relative to SL-C5 [%] SL-C5 — SL-73 77 SL-74 73 SL-75 69 SL-76 71 SL-77 74 SL-78 68 SL-79 66 SL-80 72 SL-81 75

Example 19

[0255] A quantitative Humi-Dome study was carried out as described in Example 18 with the difference that glyphosate-K was added to the tank-mixes. SL-C was used as a comparative sample consisting of dicamba-K in water. The application rate of glyphosate was 1120 grams of acid equivalents per hectare. After 24 hours, filters were collected, extracted and analyzed for dicamba content using gas-chromatography coupled mass spectrometry. The total amount of dicamba captured was then divided by total volume of the air flow through the filter to calculate the relative reduction of dicamba captured in the filter compared with SC-C.sub.6 as summarized in Table AE.

TABLE-US-00027 TABLE AE reduction of dicamba captured in filter compared with SL-C6 as measured in Humi-Dome assay [%]. Reduction of dicamba captured in filter relative to SL-C6 with Soluble Concentrate glyphosate-K [%] SL-C6 with glyphosate-K — SL-77 with glyphosate-K 46 SL-79 with glyphosate-K 36 SL-80 with glyphosate-K 54 SL-81 with glyphosate-K 27