Composition containing a pesticide and a vinylimidazol terpolymer

Abstract

The present invention relates to an agrochemical composition containing a pesticide and a copolymer, which contains in polymerized form at least 20 wt % vinylimidazol and/or a quaternized vinylimidazol, an acidic comonomer, and a hydrophobic comonomer, which comprises C.sub.1-22 alkyl (meth)acrylate, mono C.sub.1-22 alkyl terminated poly(ethylene glycol) (meth)acrylate, vinyl ester of aliphatic C.sub.1-32 carboxylic acids, or vinyl C.sub.1-4 alkyl ether. It further relates to a method for preparing said composition by mixing the pesticide and the copolymer; and to a use of said copolymer as dispersing agent in a composition containing a pesticide. In addition it relates to a method for controlling phytopathogenic fungi and/or undesired plant growth and/or undesired attack by insects or mites and/or for regulating the growth of plants, where said composition is allowed to act on the particular pests, their habitat or the plants to be protected from the particular pest, the soil and/or on undesired plants and/or the useful plants and/or their habitat. Finally, it relates to seed containing the said composition.

Claims

1. An agrochemical aqueous composition comprising a pesticide and a copolymer comprising a) at least 20 wt % vinylimidazol and/or a quaternized vinylimidazol, b) an acidic comonomer, and c) up to 30 wt % of a hydrophobic comonomer, which comprises C.sub.1-22 alkyl (meth)acrylate, mono C.sub.1-22 alkyl terminated poly(ethylene glycol) (meth)acrylate, vinyl ester of aliphatic C.sub.1-32 carboxylic acids, or vinyl C.sub.1-4 alkyl ether, wherein the pesticide is at least 80% dispersed in the aqueous composition and has a solubility in water of up to 10 g/l at 20° C., and wherein the composition comprises at least 5 wt % of a dissolved salt.

2. The composition according to claim 1, wherein the acidic comonomer comprises a carboxylic acid unit, a sulfonic acid unit or a salt thereof.

3. The composition according to claim 1, wherein the acidic comonomer is acrylic acid or methacrylic acid.

4. The composition according to claim 1, wherein the copolymer comprises a) 20 to 80 wt % vinylimidazol or a quaternized vinylimidazol, b) 1 to 20 wt % acidic comonomer, and c) 1 to 25 wt % hydrophobic comonomer.

5. The composition according to claim 1, wherein the copolymer further comprises a hydrophilic comonomer d), which comprises N-vinyllactam, (meth)acrylamide, poly(ethylene glycol) (meth)acrylate, an N—C.sub.1-8 alkyl acrylamide, or mixtures thereof.

6. The composition according to claim 5, wherein the hydrophilic comonomer is a N-vinyllactam.

7. The composition according to claim 1, wherein the copolymer further comprises 5 to 70 wt % hydrophilic comonomer d).

8. The composition according to claim 1, wherein the copolymer comprises vinylimidazol and quaternized vinylimidazol, and wherein at least 20% of the vinylimidazol is converted to the quaternized vinylimidazol.

9. The composition according to claim 1, wherein the hydrophobic comonomer comprises mono C.sub.12-20 alkyl terminated poly(ethylene glycol) (meth)acrylate.

10. The composition according to claim 1, wherein the dissolved salt comprises an ionic pesticide.

11. A method for preparing the composition as defined in claim 1 by mixing the pesticide and the copolymer.

12. A method for controlling phytopathogenic fungi and/or undesired plant growth and/or undesired attack by insects or mites and/or for regulating the growth of plants, where the composition as defined in claim 1 is allowed to act on the particular pests, their habitat or the plants to be protected from the particular pest, the soil and/or on undesired plants and/or the useful plants and/or their habitat.

13. The method of claim 12, wherein the acidic comonomer comprises a carboxylic acid unit, a sulfonic acid unit or a salt thereof.

14. The method of claim 12, wherein the acidic comonomer is acrylic acid or methacrylic acid.

15. The method of claim 12, wherein the copolymer comprises a) 20 to 80 wt % vinylimidazol or a quaternized vinylimidazol, b) 1 to 20 wt % acidic comonomer, and c) 1 to 25 wt % hydrophobic comonomer.

16. The method of claim 12, wherein the copolymer further comprises a hydrophilic comonomer d), which comprises N-vinyllactam, (meth)acrylamide, poly(ethylene glycol) (meth)acrylate, an N—C.sub.1-8 alkyl acrylamide, or mixtures thereof.

17. The method of claim 16, wherein the hydrophilic comonomer is a N-vinyllactam.

18. The method of claim 12, wherein the copolymer further comprises 5 to 70 wt % hydrophilic comonomer d).

19. Seed treated with the composition of claim 1.

Description

EXAMPLES

(1) Solvesso® 200 ND: Hydrocarbon fluid, aroamtic content>99%, initial boiling point about 242° C., final boiling point about 299° C., commercially available from Exxon Mobile. Dispersant A: Ammonium salt of polyarylphenylethersulfate. Dispersant B: 2-Ethylhexyl glucopyranoside.
Comonomers a): VI: vinylimidazol QVI: quaternized vinylimidazol (quaternized with gaseous methyl chloride)
Acidic Comonomers b): MAS: methacrylic acid
Hydrophobic comonomers c): nBA: n-butyl acrylate LA: lauryl acrylate, comprising 50-75 wt % dodecyl acrylate and 25-50 wt % tetradecyl acrylate. 2-PHA: 2-propylheptyl acrylate LUMA: acrylic acid ester of linear C16/18 fatty alcohol terminated poly(ethylene glycol) with about 25 mol ethylene glycol units per molecule. PEGMA: Monomethyl poly(ethylene glycol) methacrylate, mol weight of PEG was about 350 g/mol
Hydrophilic Comonomers d): VP: N-vinyl pyrrolidone

Example 1—Composition of Polymers

(2) The following copolymers were prepared with a composition of comonomers as described in Tables 1 to 3 by precipitation polymerisation or polymerisation in solution according to known methods (e.g. described in WO 2007/010034, DE 10 2005 046 916, or EP 0 913 143).

(3) TABLE-US-00001 TABLE 1 Composition of polymers (all values in wt %), prepared by precipitation polymerisation. No. VI QVI MAS LA nBA LUMA VP 1 70 — 10 — 20 — — 2 25 — 5 — 20 — 50 3 25 — 5 10 — — 60 4 35 — 5 — — 5 55 5 30 — 7.5 — — 7.5 55 6 20 — 5 — — 5 70 7 25 — 5 — 20 — 50 8 70 — 5 — 20 5 — 9 60 — 5 — 20 5 10 10  40 — 5 — 20 5 30 11.sup.a) 9 27 3.6 — — 3.6 56.8 12  9 27 3.6 — — 3.6 56.8 .sup.a)including 0.1 wt % PETAE (pentaerythritol ally ether).

(4) TABLE-US-00002 TABLE 2 Composition of polymers (all values in wt %), prepared by solution polymerisation. No. VI QVI MAS LUMA VP 13 30 — 7.5 7.5 55 14 30 — 7.5 7.5 55 15 30 — 5 5 60 16 15 20 5 5 55 17 20 — 15 5 60 18 20 10 5 5 60 19 10 20 5 5 60 20.sup.a) 20 — 5 5 70 21.sup.a) 20 10 5 5 60 .sup.a)including 0.05 wt % PETAE.

(5) TABLE-US-00003 TABLE 3 Composition of polymers (all values in wt %). No. VI MAS 2-PHA LUMA PEGMA nBA VP 22 20 5 — 5 — — 70 23 70 5 — 5 — — 20 24 70 2.5 — 2.5 — — 25 25 60 2.5 — 2.5 — — 35 26 20 5 — 5 — 5 65 27 45 5 10 — — — 40 28 30 5 15 — — — 50 29 20 5 15 — — — 60 30 10 5 15 — — — 70 31 10 5 20 — — — 65 32 45 5 10 — — — 40 33 45 5 10 — — — 40 34 40 10 10 — — — 40 35 25 25 10 — — — 40 36 10 40 10 — — — 40 37 25 25 10 — — — 40 38 45 5 10 — 3 — 37 39 45 5 10 — 6 — 34 40 45 5 10 — 9 — 31

Example 2—Preparation of Agrochemical Formulations A to C

(6) The Compositions 1) and 2) were prepared as follows:

(7) Composition 1): Glyphosate isopropylamine salt solution (67.5 wt %, corresponding to about 50 wt % glyphosate free acid), or Roundup® Ultramax (aqueous solution comprising 51 wt % glyphosate isopropylamin salt and 7.5% ethoxylated amine, CAS no. 68478-96-6) was mixed with water and polymer from example 1 and optionally Dispersant A and Dispersant B, and the mixture was intensively mixed for an hour with a dissolver disc.

(8) Composition 2): Pyraclostrobin was dissolved in benzylalcohol or in Solvesso® 200 ND.

(9) The Composition 1) and Composition 2) were mixed. The final mixture was intensively mixed at 50° C. for 1 hour with a dissolver disc until a homogeneous emulsion was obtained. The final composition of the formulations A to C is summarized in Table 4. Samples were taken for storage tests (Example 3). In total 15 formulations of each Formulation A-C were prepared with the polymer no. 1-15 according to Table 1 and 2.

(10) TABLE-US-00004 TABLE 4 Composition of formulations A to C with each polymer no 1-15 Formulation A B C Glyphosate isopropylamine 70%  — 70% salt solution Roundup ® Ultramax — 70% — Polymer from Example 1 2%  2%  2% Dispersant A 5% — — Dispersant B 3% — — Solvesso ® 200 ND — 16% 16% Benzylalcohol 16%  — — Pyraclostrobin 3.2%   3.2%  3.2%  Water up to 100% up to 100% up to 100%

Example 3—Storage Stability

(11) The formulations of example 2 were stored for seven days at 40° C. without moving them. Afterwards, they were visually inspected for phase separation (Table 5 and 6; “Stable” indicates that no phase separation was found).

(12) TABLE-US-00005 TABLE 5 Storage stability for polymers of Table 1 and 2. The first column represents the number of the polymer sample as indicated in Table 1 and 2 (n.d.: not determined). Polymer No. Formulation A Formulation B Formulation C 1 Stable n.d. Stable 2 Stable n.d. Stable 3 Stable n.d. Stable 4 Stable n.d. Stable 5 Stable n.d. Stable 6 n.d. n.d. Stable 7 n.d. n.d. Stable 8 n.d. n.d. Stable 9 n.d. n.d. Stable 10 n.d. n.d. Stable 11 Stable Stable Stable 12 Stable Stable Stable 13 Stable Stable n.d. 14 Stable Stable n.d. 15 Stable Stable n.d.

(13) TABLE-US-00006 TABLE 6 Storage stability for polymers of Table 3. The first column represents the number of the polymer sample as indicated in Table 3 (n.d.: not determined). Polymer No. Formulatin A Formulation B 22 stable n.d. 23 stable n.d. 24 stable n.d. 25 stable n.d. 26 stable stable 27 stable n.d. 28 stable n.d. 29 stable n.d. 31 n.d. stable 32 stable stable 33 stable stable 34 stable n.d. 35 stable n.d. 37 stable n.d. 38 stable stable 39 stable stable

Example 4—Preparation of Agrochemical Formulation D to G

(14) The Compositions 3) and 4) were prepared as follows:

(15) Composition 3): The polymer from Example 1 were dissolved in water and Pesticide Solution A (an aqueous solution containing 10 wt % mepiquat chloride and 31 wt % of a dissolved ionic pesticide). The mixture was intensively mixed for an hour with a dissolver disc.

(16) Composition 4): Pyraclostrobin was dissolved in N,N-dimethyldodecanamide, Solvesso® 200 ND, benzyl alcohol or 2-ethyxlhexyl-(5)-lactate.

(17) The Composition 3) and Composition 4) were mixed. The final mixture was intensively mixed at 50° C. for 1 hour with a dissolver disc until a homogeneous emulsion was obtained. The final composition of the formulations D to G is summarized in Table 7. Samples were taken for storage tests (Example 5). Formulations of each Formulation D-G were prepared with the polymers according to Tables 1-3.

(18) TABLE-US-00007 TABLE 7 Formulation D E F G Pesticide Solution A 70% 70% 70% 70% Polymer from Example 1  2%  2%  2%  2% Solvesso ® ND 200 16% — — — N,N-Dimethyldodecanamide — 16% — — 2-Ethyxlhexyl-(S)-lactate — — 16% — Benzyl alcohol — — — 16% Pyraclostrobin 3.2%  3.2%  3.2%  3.2%  Water up up up up to 100% to 100% to 100% to 100%

Example 5—Storage Stability

(19) The formulations of example 4 were stored for seven days at 40° C. without moving them. Afterwards, they were visually inspected for phase separation.

(20) TABLE-US-00008 TABLE 8 Storage stability for polymers of Table 1 and 2. The first column represents the number of the polymer sample as indicated in Table 1 and 2 (n.d.: not determined). Polymer No. Formulation D Formulation E Formulation F 11 Stable Stable Stable 12 Stable Stable Stable

(21) TABLE-US-00009 TABLE 9 Storage stability for polymers of Table 3. The first column represents the number of the polymer sample as indicated in Table 3 (n.d.: not determined). Polymer No. Formulation G 26 stable 32 stable 33 stable 35 stable 37 stable 38 stable 39 stable 40 stable