STABLE AQUEOUS SUSPENSION FORMULATIONS

Abstract

Described herein is a stable aqueous suspension including dispersed particles of a beneficial effect material such as a pesticide, a relatively high amount of adjuvant and a compatibilizer. Also described herein are a process for preparing the stable aqueous suspension and products of said process.

Claims

1. A stable aqueous suspension comprising: (i) dispersed particles of at least one beneficial effect material, wherein the dispersed particles have a particle size distribution characterized by D90 of 50 μm or less; (ii) from 10 to 60% by weight, based on the total weight of the suspension, of at least one adjuvant selected from the group consisting of compounds of formula R.sup.1—O—(R.sup.2—O).sub.n—R.sup.3, wherein R.sup.1 is C.sub.8-C.sub.22-alkyl or C.sub.8-C.sub.22-alkenyl, each R.sup.2 is independently selected from the group consisting of C.sub.2-C.sub.5-alkylene radicals, with the proviso that at least one R.sup.2 is other than a C.sub.2-alkylene radical when R.sup.1 is C.sub.9-C.sub.15-alkyl or C.sub.9-C.sub.15-alkenyl; n is an integer of from 1 to 35, and R.sup.3 is H or C.sub.1-C.sub.5-alkyl, and mixtures of such compounds; and (iii) at least one compatibilizer selected from the group consisting of: (a) ether compounds of formula R.sup.4—O—(CH.sub.2—CH.sub.2—O).sub.m—H, wherein R.sup.4 is C.sub.6-C.sub.8-alkyl, m is an integer of from 1 to 15, and mixtures of such ether compounds; (b) sulfated compounds of formula R.sup.6—O—(R.sup.5—O).sub.p—S(O).sub.2—O.sup.− M.sup.+, wherein R.sup.5 is independently selected from the group consisting of C.sub.2-C.sub.5-alkylene radicals, p is an integer of from 0 to 15, R.sup.6 is C.sub.6-C.sub.14-alkyl, and M.sup.+ is an alkali ion or ammonium ion, and mixtures of such sulfated compounds; and (c) mixtures of at least one ether compound as defined in (a) and at least one sulfated compound as defined in (b).

2. The aqueous suspension of claim 1, comprising a preservative and an anti-freezing agent.

3. The aqueous suspension of claim 1, wherein the at least one adjuvant is selected from the group consisting of compounds of formula R.sup.1—O—(R.sup.2—O).sub.n—R.sup.3, wherein R.sup.1 is C.sub.8-C.sub.18-alkyl or C.sub.8-C.sub.18-alkenyl; each R.sup.2 is independently selected from the group consisting of C.sub.2-C.sub.4-alkylene radicals, with the proviso that at least one R.sup.2 is other than a C.sub.2-alkylene radical when R.sup.1 is C.sub.9-C.sub.15-alkyl or C.sub.9-C.sub.15-alkenyl; n is an integer of from 6-20, and R.sup.3 is H or C.sub.1-C.sub.4-alkyl, and mixtures of such compounds; and wherein the at least one compatibilizer selected from the group consisting of: (a) ether compounds of formula R.sup.4—O—(CH.sub.2—CH.sub.2—O).sub.m—H, wherein R.sup.4 is C.sub.6-C.sub.5-alkyl, m is an integer of from 4-10, and mixtures of such ether compounds; (b) sulfated compounds of formula R.sup.6—O—(R.sup.5—O).sub.p—S(O).sub.2—O.sup.− M.sup.+, wherein R.sup.5 is independently selected from the group consisting of C.sub.2-C.sub.5-alkylene radicals, p is an integer of from 0 to 5, R.sup.6 is C.sub.8-C.sub.14-alkyl, and M.sup.+ is an alkali ion or ammonium ion, and mixtures of such sulfated compound; and (c) mixtures of at least one ether compound as defined in (a) and at least one sulfated compound as defined in (b).

4. The aqueous suspension of claim 1, wherein the aqueous suspension comprises a dispersant.

5. The aqueous suspension of claim 1, wherein the aqueous suspension comprises propylene glycol.

6. The aqueous suspension of claim 1, wherein the at least one beneficial effect material is selected from the group consisting of agrochemically active agents, pharmaceutically active agents, and cosmetic agents.

7. The aqueous suspension of claim 1, wherein the at least one adjuvant is selected from the group consisting of compounds of formula R.sup.1—O—(R.sup.2—O).sub.n—R.sup.3, wherein R.sup.1 is C.sub.15-C.sub.19-alkyl or C.sub.15-C.sub.19-alkenyl, each R.sup.2 is independently selected from the group consisting of C.sub.2-C.sub.4-alkylene radicals, with the proviso that at least one R.sup.2 is other than a C.sub.2-alkylene radical when R.sup.1 is C.sub.9-C.sub.15-alkyl or C.sub.9-C.sub.15-alkenyl; n is an integer of from 16 to 20, and R.sup.3 is H or butyl; or wherein R.sup.1 is C.sub.7-C.sub.9-alkyl or C.sub.7-C.sub.9-alkenyl, each R.sup.2 is independently selected from the group consisting of C.sub.2-C.sub.4-alkylene radicals, with the proviso that at least one R.sup.2 is other than a C.sub.2-alkylene radical when R.sup.1 is C.sub.9-C.sub.15-alkyl or C.sub.9-C.sub.15-alkenyl; n is an integer of from 13 to 15, and R.sup.3 is H; and mixtures of such compounds.

8. The aqueous suspension of claim 1, wherein the at least one adjuvant is selected from the group consisting of compounds of formula R.sup.1—O—(R.sup.2—O).sub.n—R.sup.3, wherein (a) R.sup.1 is straight or branched C.sub.8-C.sub.15-alkyl, each R.sup.2 is independently selected from the group consisting of C.sub.2-C.sub.5-alkylene radicals, with the proviso that at least one R.sup.2 is other than a C.sub.2-alkylene radical, n is an integer of from 1 to 25, and R.sup.3 is H, or (b) R.sup.1 is straight or branched C.sub.16-C.sub.22-alkyl or straight or branched C.sub.16-C.sub.22-alkenyl, R.sup.2 and n are as defined in claim 1, and R.sup.3 is C.sub.1-C.sub.5-alkyl, and mixtures of such compounds.

9. The aqueous suspension of claim 1, wherein the at least one adjuvant is selected from the group consisting of compounds of formula R.sup.1—O—(R.sup.2—O).sub.n—R.sup.3, wherein (a1) R.sup.1 straight or branched C.sub.8-C.sub.15-alkyl, (R.sup.2—O).sub.n is a polymeric group of 1-10 ethylene oxide radicals and 1-5 butylene oxide radicals, and R.sup.3 is H, or (a2) R.sup.1 straight or branched C.sub.8-C.sub.15-alkyl, (R.sup.2—O).sub.n is a polymeric group of 1-10 ethylene oxide radicals and 1-10 propylene oxide radicals, and R.sup.3 is H, or (a3) R.sup.1 is straight or branched C.sub.16-C.sub.18-alkyl or straight or branched C.sub.16-C.sub.18-alkenyl, (R.sup.2—O).sub.n is a polymeric group of 1-25 ethylene oxide radicals, and R.sup.3 is C.sub.1-C.sub.4-alkyl, and mixtures of such compounds.

10. The aqueous suspension of claim 1, comprising, based on the total weight, from 2.0 to 12% by weight of the at least one compatibilizer.

11. The aqueous suspension of claim 1, wherein the at least one compatibilizer is selected from the group consisting of: (a) ether compounds of formula R.sup.4—O—(CH.sub.2—CH.sub.2—O).sub.m—H, wherein R.sup.4 is C.sub.6-C.sub.7-alkyl, and m is an integer of from 1 to 10, and mixtures of such ether compounds; (b) sulfated compounds of formula R.sup.6—O—(R.sup.5—O).sub.p—S(O).sub.2—O.sup.− M.sup.+, wherein R.sup.5 is independently selected from the group consisting of ethylene, propylene and butylene, p is an integer of from 0 to 10, R.sup.6 is straight or branched C.sub.7-C.sub.9-alkyl, and M.sup.+ is an alkali ion or ammonium ion, and mixtures of such sulfated compounds; and (c) mixtures of at least one ether compound as defined in (a) and at least one sulfate compound as defined in (b).

12. The aqueous suspension of claim 1, wherein the at least one compatibilizer is selected from the group consisting of: sulfated compounds of formula R.sup.6—O—(R.sup.5—O).sub.p—S(O).sub.2—O.sup.− M.sup.+, wherein R.sup.5 is independently selected from the group consisting of ethylene, propylene and butylene, p is an integer of from 0 to 4, R.sup.6 is straight C.sub.7-C.sub.15-alkyl, and M.sup.+ is an alkali ion or ammonium ion, and mixtures of such sulfated compounds.

13. The aqueous suspension of claim 1, wherein the at least one compatibilizer is selected from the group consisting of: (a) C.sub.6H.sub.13—O—(CH.sub.2—CH.sub.2—O).sub.5—H, (b) sodium 2-ethyl hexyl sulfate or ammonium 2-ethyl hexyl sulfate, and (c) mixtures of (a) and (b).

14. The aqueous suspension of claim 1, wherein the amount of the at least one beneficial effect material is from 5 to 30% by weight, based on the total weight of the aqueous suspension.

15. The aqueous suspension of claim 2, wherein the agrochemically active agent is a pesticide.

16. The aqueous suspension of claim 15, wherein the pesticide is selected from the group consisting of strobilurin fungicides and mixtures thereof.

17. The aqueous suspension of claim 16, wherein the pesticide is selected from the group consisting of azoxystrobin, fluoxastrobin, trifloxystrobin, kresoxim methyl, picoxystrobin, and mixtures thereof.

18. The aqueous suspension of claim 1, comprising, based on its total weight, at least 20% by weight of water.

19. The aqueous suspension of claim 1, wherein the sum of the at least one beneficial effect material, the at least one adjuvant, the at least one compatibilizer and the water comprised in the aqueous suspension makes up at least 85% by weight of the total weight of the aqueous suspension.

20. A process for preparing a stable aqueous suspension, the process comprising the steps: (A) (1) mixing an aqueous suspension of particles of at least one beneficial effect material with at least one compatibilizer to obtain a compatibilized beneficial effect material suspension; and (2) combining the compatibilized beneficial effect material suspension with at least one adjuvant to obtain an aqueous suspension; or (B) (1) adding to a solution of at least one compatibilizer at least one adjuvant; and (2) combining the compatibilized adjuvant solution with an aqueous suspension of particles of at least one beneficial effect material to obtain an aqueous suspension; wherein the at least one compatibilizer is selected from the group consisting of: (a) ether compounds of formula R.sup.4—O—(CH.sub.2—CH.sub.2—O).sub.m—H, wherein R.sup.4 is C.sub.6-C.sub.8-alkyl, m is an integer of from 1 to 15, and mixtures of such ether compounds; (b) sulfated compounds of formula R.sup.6—O—(R.sup.5—O).sub.p—S(O).sub.2—O.sup.− M.sup.+, wherein R.sup.5 is independently selected from the group consisting of C.sub.2-C.sub.5-alkylene radicals, p is an integer of from 0 to 15, R.sup.6 is C.sub.6-C.sub.14-alkyl, and M.sup.+ is an alkali ion or ammonium ion, and mixtures of such sulfated compounds; and (c) mixtures of at least one ether compound as defined in (a) and at least one sulfated compound as defined in (b); and wherein the at least one adjuvant is selected from the group consisting of compounds of formula R.sup.1—O—(R.sup.2—O).sub.n—R.sup.3, wherein R.sup.1 is C.sub.8-C.sub.22-alkyl or C.sub.8-C.sub.22-alkenyl, each R.sup.2 is independently selected from the group consisting of C.sub.2-C.sub.5-alkylene radicals, with the proviso that at least one R.sup.2 is other than a C.sub.2-alkylene radical when R.sup.1 is C.sub.9-C.sub.15-alkyl or C.sub.9-C.sub.15-alkenyl; n is an integer of from 1 to 35, and R.sup.3 is H or C.sub.1-C.sub.5-alkyl, and mixtures of such compounds.

21. The process of claim 20, wherein the amount of the at least one adjuvant used is from 10 to 60% by weight, based on the total weight of the obtained aqueous suspension of the beneficial effect material.

22. The process of claim 20, wherein the amount of the at least one beneficial effect material is from 5 to 30% by weight, based on the total weight of the obtained aqueous suspension of the beneficial effect material.

23. The process of claim 20, wherein the at least one beneficial effect material is an agrochemically active agent.

24. The process of claim 20, wherein the obtained aqueous suspension obtained in of the beneficial effect material comprises, based on its total weight, at least 20% by weight of water.

25. The process of claim 20, wherein the sum of the at least one beneficial effect material, the at least one adjuvant, the at least one compatibilizer and the water comprised in the obtained aqueous suspension of the beneficial effect material makes up at least 85% by weight of the total weight of the aqueous suspension.

26. A stable aqueous pesticide-adjuvant suspension obtainable obtained by the process of claim 20.

Description

EXAMPLES

[0560] Method (I): Particle Size Analysis According to CIPAC MT 187

[0561] 1.0 ml of the sample (suspension) was stirred into 9 ml of fully demineralized water using a magnetic stirrer. Specific amounts of this diluted sample were added to the Malvern Master Sizer Dispersing Unit (Hydro MV) until a laser shadowing of 15% (+/−3%) was reached. Within the dispersing unit, the sample was diluted in 120 ml of fully demineralized water and pumped through the measuring cell of the Malvern Mastersizer 3000 (Malvern Pananalytical GmbH, Germany) that used a 632.8 nm laser (4 mW He—Ne) for analysis. The sample and the fully demineralized water used for the dilution were at room temperature.

[0562] Particle size distribution, including D10, D50 and D90 values, was calculated using the Fraunhofer model as known in the art. See, e.g., ISO 13320-1:1999(E).

[0563] Method (II): Accelerated Storage Test According to CIPAC MT 46.3

[0564] About 50 ml of the sample (suspension) were placed in a 100 ml glass bottle fitted with screw cap and polyethylene inserts, and kept in an oven at the specified temperature (+/−2° C.) for the defined period of time. Then the bottle was removed from the oven and allowed to reach room temperature before further analysis.

Example A: Preparation of Suspension Concentrates

[0565] The ingredients of the suspension concentrates are summarized in Table 1 below.

[0566] Suspensions concentrates were prepared by grinding the ingredients of “part A” (see Table 1) in a bead mill with zirconium oxide grinding beads such that the dispersed pesticide particles reach a particle size distribution characterized by a D90 of ≤10 μm and a D50≤3 μm. Particles analysis was done according to method (I) above. Then the thus obtained pesticide suspension concentrate was mixed with the compatibilizer (see “part B” of Table 1). Finally, the adjuvant (“part C” of Table 1) was added.

TABLE-US-00005 TABLE 1 Composition of suspension concentrates [% by weight] (relative to the total weight of the suspension concentrate) Examples Reference Examples ingredients 1 2 3 4 5 6 R1 R2 R3 R4 part A water 26.84 21.20 56.84 51.20 46.84 41.20 81.84 31.84 61.84 51.84 azoxystrobin 15.00 15.00 15.00 15.00 15.00 15.00 15.00 15.00 15.00 15.00 (pesticide) Dispersant.sup.2) 2.50 2.50 2.50 2.50 2.50 2.50 2.50 2.50 2.50 2.50 Agnique DFM 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 0.30 (anti-foaming agent) 2% by weight 0.36 0.36 0.36 0.36 0.36 0.36 0.36 0.36 0.36 0.36 xanthan gum in water (thickener) part B hexanol-5EO.sup.1) 5.00 — 5.00 — 5.00 — — — — — (compatibilizer) 47% by weight — 10.64 — 10.64 — 10.64 — — — — sodium 2-ethylhexyl sulfate in water (compatibilizer) part C Adjuvant 1.sup.3) 50.00 50.00 — — — — — 50.00 — — Adjuvant 2.sup.3) — — 20.00 20.00 — — — — 20.00 — Adjuvant 5.sup.3) — — — — 30.00 30.00 — — — 30.00 .sup.1)C.sub.6H.sub.13-O-(CH.sub.2-CH.sub.2-O).sub.5-H .sup.2)block copolymer, central with polypropylene glycol, flanked with two polyethylene glycol groups .sup.3)Adjuvants as described in Table A above

Example B: Stability Assessment of Suspension Concentrates

[0567] The stability of the suspension concentrates obtained in example A was assessed by performing a particle size distribution analysis so as to determine the D90, D50 and D10 values of the dispersed particles (see method (I) above). Storage stability was assessed as described in method (II) above.

[0568] B1) Effect of Adjuvant on the Stability of Pesticide Suspension Concentrates

[0569] The effect of relatively high amounts of adjuvants was examined by comparing the pesticide suspension concentrate of reference example R1 with the pesticide-adjuvant suspension concentrates of reference examples R2, R3 and R4. To this end, the particle size distribution analysis of the suspension concentrates was performed after keeping the suspension concentrates (subsequent to their preparation) at room temperature for 24 h.

[0570] The pesticide suspension concentrate of reference example R1 was stable, i.e. the D10, D50 and D90 values remained the same over the 24 h storage period at room temperature. The addition of adjuvants rendered the pesticide suspension concentrate unstable, i.e. caused significant aggregation (see Table 2).

TABLE-US-00006 TABLE 2 Particle size distribution after 24 h at room temperature R1 R2 R3 R4 appearance very low medium high high viscosity viscosity viscosity viscosity D10 [μm] 0.53 0.87 0.78 1.09 D50 [μm] 1.23 2.93 2.40 6.12 D90 [μm] 2.80 61.50 30.60 38.10

[0571] B2) Effect of Compatibilizer on the Stability of Pesticide-Adjuvant Suspension Concentrates

[0572] The effect of compatibilizer was examined by comparing the pesticide suspension concentrate of reference example R1 with the pesticide-adjuvant suspension concentrates of examples 1-6. To this end, the particle size distribution analysis of the suspension concentrates was performed after keeping the suspension concentrates (subsequent to their preparation) at 54° C. for 2 weeks. This type of incubation at elevated temperature is for faster aging so as to mimic a two-year storage at room temperature.

[0573] The pesticide suspension concentrate of reference example R1 remained stable, i.e. the D10, D50 and D90 values remained basically the same over the two-week storage period (data not shown). A comparison with the reference data in Table 2 shows that the addition of compatibilizer (hexanol-5EO or sodium 2-ethylhexyl sulfate) counteracted the adjuvant-induced aggregation (see Tables 3, 4 and 5). The adjuvants are as described in Table A above.

TABLE-US-00007 TABLE 3 Particle size distribution after 2 weeks at 54° C., adjuvant = Adjuvant 1.sup.1) Reference Examples Examples R1.sup.# R2.sup.# 1 2 appearance very low medium low viscosity low viscosity viscosity viscosity D10 [μm] 0.53 0.87 0.74 0.76 D50 [μm] 1.23 2.93 2.09 2.18 D90 [μm] 2.80 61.50 4.48 5.86 .sup.#data copied from Table 2, reference examples kept for 24 h at room temperature .sup.1)Adjuvants are as described in Table A above

TABLE-US-00008 TABLE 4 Particle size distribution after 2 weeks at 54° C., adjuvant = Adjuvant 2.sup.1) Reference Examples Examples R1.sup.# R3.sup.# 3 4 appearance very low high viscosity very low very low viscosity viscosity viscosity D10 [μm] 0.53 0.78 0.76 0.63 D50 [μm] 1.23 2.40 1.98 1.36 D90 [μm] 2.80 30.60 5.63 3.55 .sup.#data copied from Table 2, reference examples kept for 24 h at room temperature .sup.1)Adjuvants are as described in Table A above

TABLE-US-00009 TABLE 5 Particle size distribution after 2 weeks at 54° C., adjuvant = Adjuvant 5.sup.1) Reference Examples Examples R1.sup.# R4.sup.# 5 6 appearance very low high viscosity low to medium low to medium viscosity viscosity viscosity D10 [μm] 0.53 1.09 0.69 0.65 D50 [μm] 1.23 6.12 2.10 1.51 D90 [μm] 2.80 38.10 4.96 5.50 .sup.#data copied from Table 2, reference examples kept for 24 h at room temperature .sup.1)Adjuvants are as described in Table A above

Example C: Preparation of Suspension Concentrates

[0574] Suspensions concentrates were prepared by grinding 40-50% azoxystrobin, 2.5% dispersant (copolymer based on vinyl acetate with alcohol-EO), 0.3% anti-foam (Agnique DFM 111 S) in a disperser “DAS 200”, Lau GmbH with glass balls (diameter: 2 or 3 mm) such that the dispersed pesticide particles reach a particle size distribution characterized by a D90 of ≤10 μm and a D50≤3 μm. Particles analysis was done according to method (III). The adjuvant was added to a solution of compatibilizer in water. After that the obtained pesticide suspension concentrate was added to the compatibilizer-adjuvant-mixture to get a concentration of 10% active at the end. Storage stability was assessed as described in method (IV).

[0575] When using compatibilizer according to the formula R.sup.6—O—(R.sup.5—O).sub.p—SO.sub.3.sup.−M.sup.+) with R6=C.sub.12/C.sub.14 linear, R5 Et, p=1, M=Na, addition of propylene glycol to the solution of compatibilizer in water facilitated the workability of the compatibilizer.

[0576] For the preparation method used in this example, typical other auxiliaries like anti-freeze, biozide and if necessary crystal growth inhibitor are typically incorporated in the adjuvant-compatibilizer mixture before adding it to the milled aqueous pesticide suspension concentrate. Finally, thickener is added to adjust the desired viscosity.

[0577] Method (III): Particle Size Analysis According to CIPAC MT 187

[0578] 1.0 ml of the sample (suspension) was stirred into 9 ml of fully demineralized water using a magnetic stirrer. Specific amounts of this diluted sample were added to the Malvern Master Sizer 3000 Dispersing Unit (Hydro MV) until a laser shadowing of 6 to 8% was reached. Within the dispersing unit, the sample was diluted in 120 ml of fully demineralized water and pumped through the measuring cell of the Malvern Mastersizer 3000 (Malvern Pananalytical GmbH, Germany) that used a 632.8 nm laser (4 mW He—Ne) for analysis. The sample and the fully demineralized water used for the dilution were at room temperature.

[0579] Particle size distribution, including D50 and D90 values, was calculated using the Fraunhofer model as known in the art. See, e.g., ISO 13320-1:1999(E).

[0580] Method (IV): Accelerated Storage Test According to CIPAC MT 46.3

[0581] About 35 ml of the sample (suspension) were shared and placed in 40 ml glass bottles fitted with screw cap and polyethylene inserts, and kept in ovens at the specified temperatures (+/−2° C.) for the defined period of time. Then the bottle was removed from the oven and allowed to reach room temperature before further analysis.

[0582] The experimental result is shown in the following table (Table 6). The adjuvants and compatibilizers are abbreviated as shown above (cf. Table A and Table B, respectively).

TABLE-US-00010 TABLE 6 w (adjuvant) w (comp.) 2 weeks (w)/RT 2 w/−10 bis 40° C. 2 w/54° C. [%] compatibilizer [%] D90 [μm] D50 [μm] D90 [μm] D50 [μm] D90 [μm] D50 [μm] 20 c 7.5 2.89 1.46 4.25 1.84 4.52 1.8 30 c 7.5 3.84 1.86 4.68 2.08 4.49 1.97 30 c plus propylene 10 3.39 1.54 3.6 1.56 4.26 1.72 glycol (PG) (2:1) 35 c/PG = 2:1 10 3.39 1.55 3.42 1.54 4.01 1.68 40 c/PG = 2:1 10 3.42 1.55 3.5 1.54 3.71 1.64 40 c/PG = 2:1 10 3.19 1.47 3.18 1.48 4.67 1.7 30 c 10 3.45 1.56 4.06 1.58 3.95 1.59 30 c 10 3.17 1.47 3.21 1.49 4.01 1.59 35 c 10 3.4 1.56 3.45 1.55 3.38 1.57 40 c 10 3.18 1.46 3.2 1.48 3.53 1.58 30 d 10 4.34 1.79 3.93 1.75 3.97 1.75 20 g 7.5 3.56 1.56 3.52 1.54 3.52 1.56 20 f 5 3.22 1.58 3.85 1.85 4.4 2.15 20 f 6 5.31 1.9 3.89 1.9 3.42 1.69 30 f 6 4.02 1.76 3.5 1.72 5.08 2.19 Adjuvant: adjuvant 6, dispersant: copolymer based on vinyl acetate with alcohol-EO; d90 < 10 μm, d50 < 3 μm Adjuvant and compatibilizer as identified above in Tables A and B, respectively w (adjuvant) w (comp.) 2 w/RT 2 w/−10 bis 40° C. 2 w/54° C. [%] compatibilizer [%] D90 [μm] D50 [μm] D90 [μm] D50 [μm] D90 [μm] D50 [μm] 10 c 7.5 3.59 1.57 3.78 1.62 3.82 1.6 20 c 7.5 3.63 1.58 3.7 1.55 3.83 1.6 30 c 7.5 3.7 1.56 3.95 1.58 4.14 1.65 Adjuvant: adjuvant 7, dispersant: copolymer based on vinyl acetate with alcohol-EO; d90 ≤ 10 μm, d50 ≤ 3 μm Adjuvant and compatibilizer as identified above in Tables A and B, respectively w (adjuvant) w (comp.) 2 w/RT 2 w/−10 bis 40° C. 2 w/54° C. [%] compatibilizer [%] D90 [μm] D50 [μm] D90 [μm] D50 [μm] D90 [μm] D50 [μm] 20 d 5 3.94 1.66 3.95 1.65 4.93 1.82 20 c 5 3.90 1.64 3.98 1.64 4.40 1.77 20 e 5 3.93 1.64 3.93 1.64 4.25 1.77 Adjuvant: adjuvant 2, dispersant: copolymer based on vinyl acetate with alcohol-EO d90 < 10 μm, d50 < 3 μm Adjuvant and compatibilizer as identified above in Tables A and B, respectively w (adjuvant) w (comp.) 2 w/RT 2 w/−10 bis 40° C. 2 w/54° C. [%] compatibilizer [%] D90 [μm] D50 [μm] D90 [μm] D50 [μm] D90 [μm] D50 [μm] 20 d 5 5.32 2.29 5.73 2.64 4.95 2.08 20 c 5 5.59 2.29 6.13 2.68 5.84 2.41 20 e 5 6.48 2.55 6.53 2.89 6.79 2.71 Adjuvant: adjuvant 2, dispersant: Na salt of alkylnaphthalene sulfonate condensate; d90 < 10 μm, d50 < 3 μm Adjuvant and compatibilizer as identified above in Tables A and B, respectively Compatibilizers according to the formula R.sup.4-O-(CH.sub.2-CH.sub.2-O).sub.m-H, wherein R4 m 2-Propylheptanol (C10-branched) 5 2-Propylheptanol (C10-branched) 8 failed as compatibilizer (used amount 5-10%) using 20-40% adjuvant 6 (as identified above in Tables A). Here, no compatibilizer- adjuvant solution was obtained, but there was a phase separation. Consequently, no SC comprising active ingredient, compatibilizer and adjuvant could be prepared and no particle size could be measured.