Copolymers of N-vinylcarboxamide and diallyldialkylammonium salt as dispersant for agrochemical formulations

Abstract

The present invention relates to a composition comprising an agrochemical active substance and a copolymer which comprises an N-vinylcarboxamide and a diallyldialkylammonium salt incorporated into the polymer. The invention furthermore relates to a method of preparing this composition; to the use of this composition for dispersing agrochemical active substances; to a method of controlling phytopathogenic fungi and/or undesired plant growth and/or undesired insect or mite attack and/or for regulating the growth of plants, wherein the 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 undesired plants and/or on the crop plants and/or on their environment; and furthermore to seed comprising the composition.

Claims

1. A composition comprising an agrochemical active substance and a copolymer which consists of 40 to 95% by weight of an N-vinylcarboxamide and 5 to 50% by weight of a diallyldialkylammonium salt incorporated into the polymer, based on the total amount of the copolymerized monomers, wherein the N-vinylcarboxamide is an N-vinyl-C.sub.1-C.sub.18-alkylcarboxamide and/or an N-vinyl-N(C.sub.1-C.sub.12-alkyl)-C.sub.1-C.sub.18-alkylcarboxamide; and wherein the diallyldialkylammonium salt corresponds to the formula (I) ##STR00003## wherein R.sup.1 and R.sup.2 independently of each other are hydrogen or C.sub.1-C.sub.4-alkyl; R.sup.3 and R.sup.4 independently of each other are alkyl, hydroxyalkyl, carboxyalkyl, carboxyamidoalkyl or alkoxyalkyl having 1 to 18 carbon atoms; and Y.sup. is an anion; wherein the agrochemical active substance comprises a) a water-insoluble first pesticide and b) a water-soluble salt of a second pesticide or water-soluble inorganic fertilizer, wherein the copolymer is in dissolved form; the composition comprises at least 5% by weight of the second pesticide or of the inorganic fertilizer; the composition is in the form of an aqueous composition; the water-insoluble first pesticide is present in the form of suspended particles and has a solubility in water of up to 10 g/l at 20 C. and the water-soluble pesticide has a solubility of more than 10 g/l at 20 C.

2. The composition according to claim 1, comprising from 1 to 20% by weight of the copolymer.

3. The composition according to claim 1, wherein the copolymer is a random copolymer.

4. The composition according to claim 1, wherein the N-vinylcarboxamide is N-vinyl-N-methylformamide, N-vinylformamide, N-vinyl-N-ethylformamide, N-vinyl-N-propylformamide, N-vinyl-N-isopropylformamide, N-vinyl-N isobutylformamide, N-vinylacetamide, N-vinyl-N-methylacetamide, N-vinylpropionamide, or N-vinyl-N-methylpropionamide, and mixtures thereof.

5. A method of controlling phytopathogenic fungi and/or undesired plant growth and/or undesired insect or mite attack and/or for regulating the growth of plants, wherein the composition according to 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 undesired plants and/or on the crop plants and/or on their environment.

6. The method of claim 5, wherein the composition comprises at least 5% by weight of the second pesticide or of the inorganic fertilizer.

7. The method of claim 5, wherein the composition is in the form of an aqueous composition, wherein the water-insoluble first pesticide is present in the form of suspended particles.

8. The method of claim 5, wherein the composition comprises from 1 to 20% by weight of the copolymer.

9. The method of claim 5, wherein the copolymer is a random copolymer.

10. The method of claim 5, where diallyldialkylammonium salt corresponds to the formula (I) ##STR00004## where R.sup.1 and R.sup.2 independently of each other are hydrogen or C.sub.1-C.sub.4-alkyl; R.sup.3 and R.sup.4 independently of each other are alkyl, hydroxyalkyl, carboxyalkyl, carboxyamidoalkyl or alkoxyalkyl having 1 to 18 carbon atoms; and Y.sup. is an anion.

11. Seed treated with the composition according to claim 1.

12. The composition according to claim 1, wherein R.sup.1 and R.sup.2 independently of each other are hydrogen or methyl.

13. The composition according to claim 1, wherein R.sup.3 and R.sup.4 are methyl.

14. The composition according to claim 1, wherein the molecular weight of the polymer is from 5,000 g/mol to 250,000 g/mol.

15. The composition according to claim 1, wherein the co-polymer comprises 0.5% to 15% wt % of the composition.

16. The composition according to claim 1, wherein the N-vinylcarboxamide is N-vinylformamide.

Description

EXAMPLES

(1) Surfactant A: Anionic surfactant, sodium salt of an alkylnaphthalenesulfonic acid, water-soluble. Surfactant B: Nonionic surfactant, alkylamine ethoxylate, water-soluble, surface tension (1 g/l water, room temperature) approximately 40 mN/m.

Example 1Copolymer A

(2) Initial charge: 216 g polyethylene glycol, average molar mass 35 000 g/mol 216 g polyethylene glycol, average molar mass 1500 g/mol 164 g propanol 0.96 g triallylamine

(3) Feed 1: 384 g N-vinylformamide 147.7 g diallyldimethylammonium chloride (DADMAC; 65% by weight form) 164 g propanol

(4) Feed 2: 2.9 g tert-butyl peroctoate 164 g propanol

(5) Feed 3: 420 g propanol

(6) Feed 4: 100 g propanol 16 g sodium methoxide (30% by weight)

(7) The homogenized initial charge was heated to 90 C. with nitrogen being passed through the system, and feed 1 was metered in over 4 hours, and 112 g of feed 2 over 5 hours. After an hour of subsequent polymerization, 55 g of feed 2 were added and polymerization was continued for a further 1.5 hours. Then, using feed 3, dilution and cooling took place. Finally, the quantity of feed 3 was removed by distillation, feed 4 was added, the batch was heated under reflux for an hour, and the distillation was repeated. This gave copolymer A, containing N-vinylformamide and DADMAC in an 80/20 weight ratio. The molar mass Mw was 151 000 g/mol, with a PDI of 7.5. The solids content was 35% by weight (120 C., 2 hours), and the pH (in 10% form) was 4.5.

Example 2Formulation

(8) 14 g of pyraclostrobin, 2 g of copolymer A from example 1, 2 g of surfactant A, 3.3 g of surfactant B, 13.1 g of glyphosate isopropylammonium salt (60% by weight in water), and 21.6 g of water were weighed into a vessel. 25 ml of glass beads (0.75-1.0 mm) were added, and an aqueous pyraclostrobin suspension was prepared by shaking on a laboratory shaker (4 h, 400 rpm). Thereafter, the glass beads were filtered off.

Example 3Formulation (Comparative Experiment)

(9) An aqueous suspension of pyraclostrobin was prepared as in example 2, the terpolymer of example 1 being replaced by A) Atlox 4915, or B) Copolymer B (acrylic acid/AMPS 70/30).

(10) Atlox 4913 is a composition comprising 33% by weight of terpolymer (reaction product of methacrylic acid, methyl methacrylate and methoxypolyethylene glycol methacrylate), 33% by weight of propylene glycol, 1% by weight of xylene and 33% by weight of water), HLB value 11-12, commercially available from Uniquema.

(11) The random copolymer B comprised the following monomers incorporated into the polymer: 70% by weight of acrylic acid and 30% by weight of the sodium salt of acrylamidopropanesulfonic acid (AMPS).

Example 4Stability Test of the Suspension

(12) The aqueous suspensions of examples 2, 3A and 3B were stored without agitation for 24 hours at room temperature and thereafter assessed visually with reference to a scale of from 1 (phase separation, no longer dispersible by shaking, clumpy) to 10 (no phase separation, highly viscous, readily dispersible).

(13) TABLE-US-00001 TABLE 1 Formulation of example Stability assessment 2 9 3A .sup.a) 8 3B .sup.a) 2 .sup.a) comparative experiment