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CN-122003169-A - Composition and method for producing the same

CN122003169ACN 122003169 ACN122003169 ACN 122003169ACN-122003169-A

Abstract

An agrochemical composition comprising a copolymer consisting of two monomers represented by the formula wherein (I) is a hydrophobic monomer and (II) is a hydrophilic monomer, wherein R 1 is selected from hydrogen or methyl, R 2 is C 1‑6 alkyl, R 3 is selected from hydrogen or methyl, R 4 is selected from-CONH m (C 1‑6 alkyl) n (wherein m=0, 1 or 2, n=0, 1 or 2), -C 5 heterocyclic ketone, -C (O) O (CH 2 CH 2 O) pH (wherein p=1 to 50), -C (O) O (CH 2 CH 2 O) p R 5 (wherein p=1 to 20 and wherein R 5 is C 1‑6 alkyl).

Inventors

  • J.A.BURNS
  • B. L. Holt
  • E. L. Keanaston
  • C.I. LINDSAY
  • M. J. Remaruk

Assignees

  • 先正达农作物保护股份公司

Dates

Publication Date
20260508
Application Date
20241004
Priority Date
20231013

Claims (15)

  1. 1. An agrochemical composition comprising: A copolymer composed of two monomers represented by the formula wherein (I) is a hydrophobic monomer and (II) is a hydrophilic monomer Wherein the method comprises the steps of R 1 is selected from hydrogen or methyl; R 2 is C 1-6 alkyl; R 3 is selected from hydrogen or methyl; r 4 is selected from: CONH m (C 1-6 alkyl) n , where m=0, 1 or 2, n=0, 1 or 2, -A C 5 -heterocyclic ketone, C (O) O (CH 2 CH 2 O) p H, where p=1 to 50, -C (O) O (CH 2 CH 2 O) p R 5 , wherein p=1 to 20 and wherein R 5 is C 1-6 alkyl.
  2. 2. The composition of claim 1, wherein the molecular weight of the polymer is 900 g to 500 000 g/mol.
  3. 3. The composition according to any one of claims 1 or 2, wherein the polymer has a ratio of monomer (I): monomer (II) of 80:20 to 20:80% w/w.
  4. 4. The composition of any of the preceding claims, wherein the polymer is a random copolymer.
  5. 5. The composition of any one of the preceding claims, further comprising a surfactant, preferably wherein the surfactant is a nonionic surfactant and/or an anionic surfactant.
  6. 6. The composition of claim 5, wherein the surfactant is present in an amount of 0.01 to 20% w/w.
  7. 7. A composition according to any preceding claim, wherein the composition comprises an active ingredient.
  8. 8. The composition of claim 7, wherein the ratio of polymer to active ingredient is 10:1 to 1:10.
  9. 9. A composition according to any preceding claim, wherein the active ingredient is present in an amount of 0.01 to 50% w/w.
  10. 10. The composition of any one of the preceding claims, comprising a non-aqueous solvent.
  11. 11. A process for preparing a polymer as defined in any one of claims 1 to 10, the process comprising Free Radical Polymerisation (FRP) or reversible addition fragmentation chain transfer polymerisation (RAFT).
  12. 12. A method of preparing the composition of any one of claims 1 to 10.
  13. 13. Use of a polymer consisting of two monomers of the formula (I) a hydrophobic monomer and (II) a hydrophilic monomer for inhibiting crystal growth formation of an active ingredient Wherein the method comprises the steps of R 1 is selected from hydrogen or methyl; R 2 is a C 1-6 alkyl group, R 3 is selected from hydrogen or methyl; r 4 is selected from: CONH m (C 1-6 alkyl) n , where m=0, 1 or 2, n=0, 1 or 2, -A C 5 -heterocyclic ketone, C (O) O (CH 2 CH 2 O) p H, where p=1 to 50, -C (O) O (CH 2 CH 2 O) p R 5 , wherein p=1 to 20 and wherein R 5 is C 1-6 alkyl.
  14. 14. Use according to claim 13, wherein the polymer is diluted in water, preferably in a solution having a pH of 8 to 14.
  15. 15. Use of a composition according to claims 1 to 10 for the treatment of weeds, pests and/or fungi.

Description

Composition and method for producing the same The present invention relates to a composition comprising a copolymer, a process for its preparation and its use. Solvent-based agrochemical formulations, such as Dispersible Concentrates (DC) and Emulsifiable Concentrates (EC), are attractive for several reasons. Such formulations are homogeneous and therefore do not require anti-settling agents. Furthermore, solvent-based formulations generally do not require antifreeze or antimicrobial agents. DC and EC formulations are very similar, both comprising the active ingredient and a suitable surfactant, all dissolved in a non-aqueous solvent. For EC formulations, the solvent must be immiscible with water, which means that these concentrates form a spontaneous emulsion upon dilution in water. For DC formulations, the solvent must be miscible with water, which means that upon dilution in water, these concentrates form a spontaneous dispersion of Active Ingredient (AI) particles in water. One particular problem associated with both solvent-based DC and EC formulations is that uncontrolled crystal growth may occur upon dilution in water. This is undesirable as such crystals may interfere with agricultural equipment by blocking the nozzle. Conventional copolymer dispersants for solving crystal growth have difficulty in solving this problem, and carboxylic acid-based dispersants can exhibit sensitivity to pH levels. In order to solve these problems, the present invention thus provides an agrochemical composition comprising: A copolymer consisting of two monomers represented by the formula wherein (I) is a hydrophobic monomer and (II) is a hydrophilic monomer: Wherein the method comprises the steps of R 1 is selected from hydrogen or methyl; R 2 is a C 1-6 alkyl group, R 3 is selected from hydrogen or methyl; r 4 is selected from: CONH m(C1-6 alkyl) n, where m=0, 1 or 2, n=0, 1 or 2, -A C 5 -heterocyclic ketone, -C (O) O (CH 2CH2O)p H, where p=1 to 50, and -C (O) O (CH 2CH2O)pR5, wherein p=1 to 20 and wherein R 5 is C 1-6 alkyl. It has surprisingly been found that the copolymer thus defined acts to reduce crystal growth in agrochemical formulations. The terms "copolymer" and "polymer" are used interchangeably herein. The copolymer is advantageously a random copolymer. Polymer R 2 may be selected from methyl (Me, CH 3), ethyl (Et, C2H 5), n-propyl (n-Pr), isopropyl (i-Pr), n-butyl (n-Bu), isobutyl (i-Bu), sec-butyl and tert-butyl (t-Bu). More preferably, R 2 is from methyl or ethyl. R 4 can be selected from the group consisting of acrylamide, pyrrolidone and thiolactone, preferably N-vinylpyrrolidone or N, N-dimethylacrylamide. More preferably, R 4 is preferably selected from: —-CON(CH3)2, -NCO (CH 2)3 (2-pyrrolidone), - (O) O (CH 2CH2O)p H, where p=1-19, such as p=2-18, p=3-17, or p=4-16, preferably p=5-15, - (O) O (CH 2CH2O)pR5) wherein p=1 to 19, such as p=2-18, p=3-17, or p=4-16, preferably p=5-15, and wherein R 5 is C 1-6 alkyl. The preferred combinations of R 1 and R 2、R3 and R 4 are as follows: Any of the preferred embodiments described herein may be combined in any fashion, but the advantageous combination of R 1、R2、R3 and R 4 is as follows: Advantageously, the molecular weight of the polymer is 900 to 500,000 g/mol, preferably 1000 to 250,000 g/mol, such as 1000 to 100,000 g/mol. Preferably, the polymer has a ratio of monomer (I) to monomer (II) of 80:20 to 20:80% w/w, more preferably 70:30 to 30:70% w/w. It has been unexpectedly found that the compositions of the present invention are particularly stable at high pH levels. Without wishing to be bound by theory, commercial polymers used for crystal growth inhibition typically contain large amounts of carboxylic acid units, and it is believed that deprotonation of these carboxylic acid units at high pH levels results in reduced stability. Surface active agent Advantageously, the composition further comprises a surfactant, preferably wherein the surfactant is a nonionic surfactant and/or an anionic surfactant. Preferably, the surfactant is present in an amount of 0.01 to 20% w/w, preferably 0.1 to 15% w/w or more preferably 0.5 to 10% w/w. In practice, dispersible Concentrates (DCs) typically contain a surfactant to uniformly and stably disperse precipitated solid particles. Suitable surfactants are surface-active compounds such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes and mixtures thereof. Such surfactants may be used as emulsifiers, dispersants, solubilizers, wetting agents, permeation enhancers, protective colloids or adjuvants. Suitable anionic surfactants are sulfonates, sulfates, phosphates, alkali metal, alkaline earth metal or ammonium salts of carboxylates, and mixtures thereof. Examples of sulfonates are alkylaryl sulfonates, diphenyl sulfonates, alpha-olefin sulfonates, lignin sulfonates, fatty acid and oil sulfonates, ethoxylated alkylphenol sulfonates, alkoxylated aryl phenol sulfonates, condensed napht