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CN-122028792-A - Use of cyclic ether derivatives as solvents

CN122028792ACN 122028792 ACN122028792 ACN 122028792ACN-122028792-A

Abstract

The present invention relates to the use of cyclic ether derivatives as polar aprotic solvents, for example for dissolving agriculturally active agents in agricultural formulations.

Inventors

  • JIANG FAN
  • S. Streve
  • PASCAL METIVIER

Assignees

  • 法国特种经营公司

Dates

Publication Date
20260512
Application Date
20231017

Claims (15)

  1. 1. Use of a compound having formula (I) as solvent in agricultural formulations (I) Wherein: -m and n are integers from 0 to 3 X and Y are independently selected from the group consisting of-CH 2-and-O- -R1, R2, R3 and R4 are independently selected from H and alkyl.
  2. 2. Use according to claim 1, wherein, in the compound of formula (I): -m or n is equal to 1, but preferably both are equal to 1, and/or X or Y is-CH 2-, but preferably both are-CH 2-, and/or -R1, R2, R3 or R4 is H, but preferably R1 to R4 are H.
  3. 3. Use according to claim 1 or 2, wherein the compound of formula (I) is BTHFE (bis (tetrahydrofurfuryl) ether).
  4. 4. Use according to any one of claims 1 to 3 for dissolving agriculturally active compounds.
  5. 5. The use according to claim 4, wherein the agriculturally active compound is selected from the group consisting of pesticides, biopesticides, fertilizers, fertilizer stabilizers, nutrients, biostimulants, plant growth regulators, natural plant defense enhancers, inoculants, and mixtures thereof.
  6. 6. The use according to claim 4 or 5, wherein the agriculturally active compound is a pesticide selected from the group consisting of herbicides, insecticides, acaricides, fungicides, algicides, molluscicides, miticides, nematicides, biocides and rodenticides and mixtures thereof.
  7. 7. The use according to any one of claims 4 to 6, wherein the agriculturally active compound is a fungicide selected from the group consisting of azoles such as prothioconazole, epoxiconazole, difenoconazole, propiconazole, cyproconazole, tebuconazole and prochloraz, strobilurins such as azoxystrobin, trifloxystrobin, picoxystrobin, fluoxastrobin, pyraclostrobin, and carboxamides such as flurbiproflumilast, fluxapyroxad, benzovindiflupyr and fluoxastrobin, and mixtures thereof.
  8. 8. The use according to claim 4 or 5, wherein the agriculturally active compound is a fertilizer stabilizer selected from the group consisting of N- (N-butyl) thiophosphoric triamide (NBPT) and dicyandiamide (DCD), and mixtures thereof.
  9. 9. Use according to any one of claims 1 to 8 in an agricultural formulation.
  10. 10. Use according to claim 9, wherein the agricultural formulation is a pesticide-containing formulation or a fertilizer formulation, preferably an efficiency-enhancing fertilizer formulation.
  11. 11. Use according to claim 9 or 10, wherein the agricultural formulation is in the form of an Emulsifiable Concentrate (EC), a concentrated emulsion in water (EW), a Microemulsion (ME), a Suspoemulsion (SE), an Oil Dispersion (OD), a Dispersible Concentrate (DC), a Suspension Concentrate (SC), a Capsule Suspension (CS), a Soluble Liquid (SL), a flowable concentrate for seed treatment (FS), preferably in the form of an Emulsifiable Concentrate (EC), a concentrated emulsion in water (EW), a Microemulsion (ME), a Suspoemulsion (SE), an Oil Dispersion (OD), a Dispersible Concentrate (DC), a Capsule Suspension (CS), a Soluble Liquid (SL), more preferably in the form of an Emulsifiable Concentrate (EC), an emulsion in water concentrate, a microemulsion concentrate, a suspoemulsion concentrate, an oil dispersion concentrate or a dispersible concentrate, and particularly preferably in the form of an emulsifiable concentrate.
  12. 12. An agricultural formulation comprising A) An agriculturally active compound as defined in any of claims 5 to 8, and B) A compound as defined in any one of claims 1 to 3; d) Optionally at least one of the co-solvents, C) Optionally at least one emulsifier and/or one surfactant, and D) Optionally water.
  13. 13. The agricultural formulation of claim 12, in the form as defined in claim 11.
  14. 14. The agricultural formulation of claim 12, comprising A) 0.01 to 90% by weight, preferably 5 to 60% by weight, relative to the total weight of the agricultural formulation, of at least one agriculturally active compound as defined in any of claims 5 to 7, preferably at least one pesticide as defined in claim 6; b) 5% to 90% by weight, preferably 10% to 90% by weight, in particular 30% to 90% by weight, for example 30% to 80% by weight, of a compound as defined in any one of claims 1 to 3, relative to the total weight of the agricultural formulation; c) 0.1 to 40% by weight, preferably 1 to 30% by weight, relative to the total weight of the agricultural formulation, of at least one co-solvent, D) 0.05 to 40% by weight, preferably 0.1 to 35% by weight, more preferably 0.5 to 30% by weight, in particular 1 to 25% by weight, for example 1 to 5% by weight, of at least one surfactant, relative to the total weight of the agricultural formulation, and E) 5 to 90% by weight, preferably 10 to 80% by weight, in particular 25 to 70% by weight, of water relative to the total weight of the agricultural formulation.
  15. 15. Use according to any one of claims 1 to 14, wherein the use of the compound of formula (I) as a solvent comprises use as a co-solvent and/or crystallization inhibitor, preferably in an agricultural formulation as defined in claims 12 to 14.

Description

Use of cyclic ether derivatives as solvents Technical Field The present invention relates to the use of cyclic ether derivatives as polar solvents, for example for dissolving agriculturally active agents in agricultural formulations. Background The industry uses a number of chemical compounds as solvents, for example for preparing chemicals and materials, for formulating chemical compounds, or for treating surfaces. Solvents are also used to formulate agricultural compounds, in particular phytosanitary active agents (fertilizers, pesticides), for example in the form of Emulsifiable Concentrates (ECs) intended to be diluted in water by the farmer before application to the field. Industries in the agricultural field try to achieve as high a concentration of the agriculturally active compound or compounds as possible in the corresponding formulation, since high concentrations of the agriculturally active compound or compounds allow for a reduction of the volume to be applied and thus require savings in terms of applied adjuvant materials as well as in terms of packaging and logistics. Thus, in principle, highly concentrated stable formulations and co-formulations with environmentally friendly adjuvants are interesting. For agriculturally active compounds having low or relatively low water solubility, it is particularly interesting to use suitable solvents for the preparation of concentrated liquid formulations in the form of Emulsifiable Concentrates (EC), concentrated emulsions in water (EW), microemulsions (ME), suspoemulsions (SE), oil Dispersions (OD), dispersible Concentrates (DC). Further details regarding the definition of the above formulation can be found in the "guidelines file （Guidance document for the generation of data on the physical, chemical and technical properties of plant protection products）" for generating data on the physical, chemical and technical characteristics of plant protection products according to the european union's meeting and the council's regulations (EC) No. 1107/2009 on putting plant protection products on the market". Such concentrated formulations of agricultural compounds are typically diluted prior to agricultural use. Dilution by farmers is usually done by mixing agrochemical formulations with water. In addition, certain solid agriculturally active compounds are often difficult to formulate. For certain agricultural compounds, it is difficult to produce concentrated formulations that are easily diluted by farmers, stable and without substantial drawbacks (actual or perceived drawbacks) in terms of safety, toxicity and/or ecotoxicity. For certain agricultural compounds, it is difficult to formulate at relatively high concentrations with sufficient stability. In particular, it is necessary to avoid the appearance of crystals, in particular at low temperatures and/or during dilution and/or during storage of the composition, in particular at low temperatures. Crystals can have deleterious effects, particularly clogging filters of devices used to spread diluted compositions, clogging spray devices, reducing the overall activity of the formulation, creating unnecessary problems with waste management procedures used to remove crystals, and/or causing maldistribution of one or more agricultural materials over the farmland. Accordingly, the agrochemical industry is continually looking for new solvents and solvent compositions having properties that are satisfactory for agricultural applications, such as good dissolution efficiency for a wide range of agricultural compounds, for example. Furthermore, the cost of the solvent compositions should generally be moderate, and preferably they should have advantageous toxicological and/or ecotoxicological characteristics, in particular low toxicity and/or low hazard potential, and/or low volatility (low VOC-volatile organic compounds) and/or advantageously high biodegradability and/or regenerability. In the field of emulsifiable concentrate formulations (EC), polar solvents suitable for dissolving some of the key active ingredients in high concentrations are needed. N-methyl-2-pyrrolidone (NMP) or N, N-dimethylacetamide are very common polar aprotic solvents that may be used for such applications. However, they are no longer used because of their poor toxicological characteristics, and alternatives are being sought. One common polar aprotic solvent used is rhodosolv PolarClean, which shows good solubility characteristics and good toxicity/eco-toxicity characteristics. However, the agricultural market is now looking for higher performance solvents with clean (clean) toxicity/eco-toxicity characteristics. Currently, there are only a limited number of commercial options for high performance solvents with clean toxicity/eco-toxicity characteristics. Examples of such solvents are N-butylpyrrolidone (NBP) and N, N-dimethyl lactamide. The three solvents mentioned above (Rhodiasolv, polar clear, N-butylpyrrolidone (NBP) and N, N-dimethyl lact