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WO2017085636A1 - Formulation de protection des cultures et procédé de préparation associé - Google Patents

Formulation de protection des cultures et procédé de préparation associé Download PDF

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Publication number
WO2017085636A1
WO2017085636A1 PCT/IB2016/056895 IB2016056895W WO2017085636A1 WO 2017085636 A1 WO2017085636 A1 WO 2017085636A1 IB 2016056895 W IB2016056895 W IB 2016056895W WO 2017085636 A1 WO2017085636 A1 WO 2017085636A1
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WO
WIPO (PCT)
Prior art keywords
pesticide
sulfuric acid
hexaconazole
crop protection
silica
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/IB2016/056895
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English (en)
Inventor
Anand Gole
Sujeet Bhoite
Mangesh Kokate
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Tata Chemicals Ltd
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Tata Chemicals Ltd
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Filing date
Publication date
Application filed by Tata Chemicals Ltd filed Critical Tata Chemicals Ltd
Publication of WO2017085636A1 publication Critical patent/WO2017085636A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/08—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing solids as carriers or diluents
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/34—Shaped forms, e.g. sheets, not provided for in any other sub-group of this main group
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

Definitions

  • the present disclosure provides a crop protection formulation and a method of preparing the same.
  • Crop protection products or pesticides are compositions based on natural product(s), chemical(s) or biological agent(s) intended to provide protection against the damaging influence of insects, weeds, and microbes.
  • the use of pesticides in the agricultural practice has become unavoidable on account of the considerable damage caused by the pests, often leading to destruction of the entire produce.
  • the use of pesticides also has serious implications on the health of humans, animals and the environment and requires careful control. Uncontrolled use of pesticides not only adds to the cost of farming but also calls for heavy investments in the research and development of new pesticide formulations in order to cope with cases of resistance development among pests to known pesticides.
  • Pesticides are categorized on the basis of their target pests, for example, insecticides (imidacloprid, flubendiamide etc), fungicide (hexaconazole, kresoxim methyl etc) and herbicide (metribuzin).
  • Imidacloprid and flubendiamide are systemic insecticide and act on termites, sucking pests and caterpillars. Due to its high water solubility and rapid hydrolysis, imidacloprid readily leaches out in soil and therefore has a short duration of action. Multiple applications are therefore required to maintain the pesticidal activity.
  • Use of flubendiamide also suffers from serious toxicity concerns.
  • Herbicides such as metribuzin are used both pre- and post-emergence in crops and are very effective in controlling annual grasses and certain broadleaf weeds. They work by inhibiting photosynthetic system, but unfortunately are also found to contaminate ground water.
  • Hexaconazole is a systemic fungicide, effective in the treatment of a number of phyto-fungal diseases. Its mode of action is the inhibition of ergosterol biosynthesis.
  • Kresoxim- methyl is another important quasi-systemic fungicide. It is also used over a range of phyto- fungal diseases. Both these fungicides pose danger in aquatic environment and need to be restricted to lower doses.
  • Nanotechnology provides an interesting agricultural tool to increase the absorption ability of plants. Nanotechnology based delivery systems will ensure a better crop protection from pests (insects, fungus, weeds etc.) without multiple pesticide applications and reduced environmental and financial burden. There is therefore a need to develop a nanotechnology based formulation which uses bio-friendly agents to enhance the uptake of pesticides.
  • a crop protection formulation comprises porous silica nanoparticles and at least one pesticide, wherein the pesticide is entrapped within pores of the silica nanoparticles and the formulation has pesticide loading of at least 0.5% (w/w).
  • a method of preparing a crop protection formulation comprises dispersing at least one pesticide in an aqueous solution of sodium silicate to obtain a precursor solution; adding sulfuric acid- surfactant mixture to the precursor solution to obtain porous silica nanoparticles entrapping at least one pesticide within its pores; and separating porous silica nanoparticles entrapping at least one pesticide within its pores, from the solution obtained in the previous step.
  • Figure 1 FTIR analysis of plain silica (curve 1), hexaconazole-silica nanocomposite with 11% loading (curve 2) and hexaconazole-silica nanocomposite with 16% loading (curve 3), in accordance with an embodiment of the present invention.
  • Figure 2A and 2B FTIR spectra of pure silica (curve 1), hexaconazole-silica nanocomposite with 38% loading (curve 2) and pure technical grade hexaconazole (curve 3) recorded in two different regions of the infrared region, in accordance with an embodiment of the present invention.
  • Figure 3 Orientation of hexaconazole on silica surface (not to scale), in accordance with an embodiment of the present invention.
  • Figure 4 Structure of the crop protection formulation in accordance with an embodiment of the present invention.
  • the present disclosure provides a crop protection formulation and a method of preparing the same.
  • the crop protection formulation comprises porous silica nanoparticles and at least one pesticide, wherein the pesticide is entrapped within pores of the silica nanoparticles and the formulation has a pesticide loading of at least 0.5% (w/w).
  • the crop protection formulation is a nanocomposite of pesticide and silica nanoparticles.
  • the crop protection formulation has a pesticide loading in the range of 0.5% to 63% (w/w). In accordance with a specific embodiment, the crop protection formulation has a pesticide loading of 5% (w/w).
  • the crop protection formulation for application to fungal or insecticidal attack on paddy, groundnut or sugarcane comprises up to 5% (w/w) of either hexaconazole or imidacloprid.
  • Entrapment of the pesticide within the pores of silica nanoparticles is a one-pot procedure wherein nano-silica synthesis and pesticide entrapment occur simultaneously.
  • the one-pot procedure comprises addition of a sulfuric acid- surfactant mixture to a sodium silicate solution comprising at least one pesticide. Crop protection formulation having high pesticide loading such as 63% (w/w) is obtained.
  • a comparison of surface area of silica nanoparticles with increasing pesticide loading showed that the surface area of silica nanoparticles was reduced.
  • a high surface area is a measure of a high porosity of the silica nanoparticles. Therefore, a reduction in surface area with increasing pesticide loading indicates that the porosity is reduced as a result of the pesticides occupying the pores. Further, an increase in porosity which led to an increase in surface area was observed following removal of pesticide by sonication in dichloromethane. This further indicates that the pesticide is entrapped within the porous matrix of silica nanoparticles. This substantiates that in the crop protection formulation pesticide and the silica nanoparticles do not have a core-shell relationship neither the pesticide is encapsulated by the silica nanoparticles.
  • the crop protection formulation comprises silica nanoparticles in a particle size range of 10 nm to 1000 nm.
  • the pesticide is any pesticide not limited to fungicides, insecticides and herbicides.
  • the pesticide is a fungicide such as hexaconazole or kresoxim methyl, insecticide such as imidacloprid or flubendiamide, herbicide such as metribuzin.
  • the crop protection formulation of the present disclosure is absorbed by the plant tissue directly and the pesticides are released within the plant cells.
  • the crop protection formulation of the present disclosure as designed is not intended to provide slow release, sustained release, delayed release or controlled release effect of pesticides from silica nanoparticles.
  • the present disclosure also provides a method of preparing a crop protection formulation.
  • the method comprises dispersing at least one pesticide in an aqueous solution of sodium silicate to obtain a precursor solution; adding sulfuric acid- surfactant mixture to the precursor solution to obtain porous silica nanoparticles entrapping at least one pesticide within its pores; and separating said porous silica nanoparticles entrapping at least one pesticide within its pores from the solution obtained in the previous step.
  • the crop protection formulation has a pesticide loading of at least 0.5% (w/w). In accordance with a specific embodiment, the crop protection formulation has a pesticide loading in the range of 0.5% to 63% (w/w).
  • the crop protection formulation for application to fungal or insect attack on paddy, groundnut or sugarcane comprises up to 5% (w/w) of either hexaconazole or imidacloprid.
  • High pressure liquid chromatography (HPLC) and Gas Chromatography (GC) analysis is used for the analysis of the pesticide content of the crop protection formulation.
  • the pesticide(s) is any pesticide not limited to fungicides, insecticides and herbicides.
  • the pesticide is a fungicide such as hexaconazole or kresoxim methyl, insecticide such as imidacloprid or flubendiamide, herbicide such as metribuzin.
  • the silica nanoparticles are in a particle size range of 10 nm to 1000 nm.
  • the aqueous solution of sodium silicate is in a concentration range of 7-14% (w/v).
  • the sodium silicate is synthesized by boiling rice husk ash in an aqueous solution of sodium hydroxide as disclosed in the Indian Patent Application No. 1510/MUM/2010, incorporated herein by reference.
  • a commercially available sodium silicate solution is used.
  • addition of sulfuric acid- surfactant mixture to the precursor solution is carried out to facilitate gel formation followed by addition of water to liquefy the gel and further addition of sulfuric acid- surfactant mixture to the liquefied gel is resumed till neutralization.
  • surfactant is selected from lignin, gelatin, octylamine, chitosan, Dioctyl sulfosuccinate sodium salt (AOT), or combinations thereof.
  • preparation of sulfuric acid- surfactant mixture of gelatin comprises addition of gelatin to sulfuric acid, heating the mixture of gelatin and sulfuric acid to enable complete dissolution of gelatin and cooling to room temperature.
  • preparation of sulfuric acid- surfactant mixture of lignin comprises addition of sodium ligno sulfonate to sulfuric acid.
  • Sodium ligno sulfonate is a water soluble form of lignin and does not require heating.
  • the sulfuric acid- surfactant mixture comprises sulfuric acid in a concentration of 1.0 M - 5 M.
  • the sulfuric acid- surfactant mixture comprises surfactant in a concentration range of 1-5% (w/w).
  • addition of sulfuric acid- surfactant mixture to the precursor solution is carried out at a rate of 5 mL/min to 100 mL/min.
  • separation of silica nanoparticles entrapping at least one pesticide within its pores from the solution is carried out by centrifugation or filtration. In accordance with an embodiment, the separation of silica nanoparticles entrapping at least one pesticide within its pores from the solution is carried out by centrifugation at an rpm speed between 4000-8000 for 5-10 minutes.
  • the method further comprises drying of silica nanoparticles entrapping at least one pesticide within its pores at a temperature of 60 °C - 90 °C .
  • the method subsequent to drying, further comprises grinding or milling of dried silica nanoparticles entrapping at least one pesticide within its pores to obtain a fine powder of silica nanoparticles.
  • the crop protection formulation obtained by the disclosed method is a nanocomposite of pesticide and silica nanoparticles.
  • EXAMPLE 1 Comparison of surface area of Hexaconazole- silica nanocomposite with an increasing pesticide loading.
  • Hexaconazole-silica nanocomposites were prepared according to the present disclosure and the surface area of the particles determined. Extraction of hexaconazole from 38% Hexaconazole-silica nanocomposite was carried out in dichloromethane by sonication for 1 hour and the surface area was again determined. The surface area data is provided below: Sr.
  • a reduction in surface area of silica nanoparticles with increasing Hexaconazole loading indicates that the pesticide particles are occupying the pores of the silica nanoparticles.
  • an increase in surface area following removal of Hexaconazole from silica nanoparticle formulation further indicates that an entrapment in the porous matrix of silica nanoparticles occurs rather than core-shell formation or encapsulation.
  • the TEM analysis shows that the formulation has particles as small as 7- 10 nm and also bigger geometries in the form of a silica matrix. This is typical for silica wherein the Si-O-Si network forms a matrix. Hexaconazole (pesticide) cannot be imaged by TEM since it is an organic molecule. TEM analysis shows particle and network structures.
  • DLS dynamic light scattering measurements
  • EXAMPLE 3 20% Hexaconazole-silica nanocomposite formulation To a 25 mL solution of 14% sodium silicate, 2.42 grams of hexaconazole (technical grade; 92% purity) was added under stirring conditions to make a precursor solution. To this, 23 mL of 1.25 M sulfuric acid containing 2% gelatin was added dropwise. (The sulfuric acid- gelatin solution was prepared by adding gelatin to sulfuric acid and heating the solution till complete dissolution of gelatin took place). Thick gel was formed when the pH reached 9.5 to 10.5. Sulfuric acid addition was stopped at this point. To this gel, 25 mL of deionized water was added and the slurry was stirred for 10 minutes.
  • EXAMPLE 7 5% Hexaconazole-silica nanocomposite formulation
  • a precursor solution 7% sodium silicate
  • hexaconazole technical grade; 92% purity
  • 230 mL of 1.25 M sulfuric acid containing 2% lignin was added dropwise.
  • sodium ligno sulfonate powder was added to sulfuric acid and the solution stirred.
  • Thick gel was formed when the pH reached 9.5 to 10.5. Sulfuric acid addition was stopped at this point.
  • 570 mL of deionized water was added and the slurry was stirred for 10 minutes.
  • the slurry was kept under stirring conditions for another 10 minutes to ensure stable pH of 6.5-7.
  • the slurry was then centrifuged and the cake obtained was dried at 90°C for a period of 12-18 hours.
  • the resulting dried cake was ground to fine powder to obtain Hexaconazole- Imidacloprid-silica nanocomposite with 12.4% hexaconazole and 10% imidacloprid loading respectively (as determined by HPLC), to give a 1.2: 1 Hexaconazole-Imidacloprid loaded silica nanoparticle formulation.
  • the yield was 130 grams.
  • the slurry was kept under stirring conditions for another 10 minutes to ensure stable pH of 6.5-7.
  • the slurry was then centrifuged and the cake obtained was dried at 90°C for a period of 12-18 hours.
  • the resulting dried cake was ground to fine powder.
  • the loading was analyzed by HPLC and was found to be 37% imidacloprid and 3% for hexaconazole respectively. The yield was 117 grams.
  • Example 15 shows the FTIR spectra of hexaconazole-silica nanocomposite in the range of 1500-500 cm "1 .
  • Curve 1 is the spectrum for plain silica nanoparticles.
  • Curve 2, 3 are spectra recorded for hexaconazole-silica samples having different loadings of hexaconazole (11% and 16% respectively).
  • a sharp feature centered at 1095 cm “1 (feature a) is a characteristic feature of Si-0 stretching vibrations and can be clearly seen in all the curves. Absence of any other band in this region indicates that there is no interaction between hexaconazole and silica matrix and the hexaconazole is merely entrapped in the pores and the silica network.
  • Figure 2B shows the characteristic methyl and methylene symmetric and anti- symmetric stretching modes of vibration in the region 2900-2800 cm “1 (curve 3 : pure hexaconazole and curve 2: hexaconazole- silica complex). These features are clearly absent in the silica spectrum (curve 1) this further substantiates that hexaconazole is trapped in silica matrix.
  • silica nanoparticles considering only the surface is 27 m 2 /g. As per the experimental BET surface area is 450 m 2 /g which is about 20 times the simple surface area. This clearly indicates that the silica particles are highly porous. Now knowing the surface area of 1 nanoparticle, it can be calculated that how many hexaconazole molecules can theoretically fit on one nanoparticle surface assuming close packing.
  • the Crystal system is Monoclinic. As shown in the scheme figure 3, the projected area of the rectangular block can either be a x b or a x c (either the structure can lie flat on the silica surface or vertical on the silica surface as shown in the figure 3)
  • projected area is either 118 A 2 or 148 A 2 .
  • projected area is either 118 A 2 or 148 A 2 .
  • one nanoparticle surface can be occupied by 26610 hexaconazole molecules; hence in 0.0874 x 10 16 nanoparticles (i.e. 1 gram of nanoparticles) will have a total of 2327 x 10 16 hexaconazole molecules.
  • Weight of this hexaconazole can be determined by calculations:
  • hexaconazole 213 g which contains Avogadro number of hexaconazole molecules (6.023 x 10 23 molecules). Hence the weight of 2327 x 10 16 hexaconazole molecules is 0.00822 grams.
  • silica nanoparticles can have a maximum of 0.0082 grams of hexaconazole. In terms of percent, this translates to 0.82%.
  • the loadings are quite high (more particularly 23%) and hence, the surface adsorption, if any, can have only 0.82% loading and the rest is all entrapped inside the silica particles.
  • Theoretical calculations indicate that the hexaconazole is not merely adsorbed on the silica surface but is entrapped within the silica matrix.
  • a crop protection formulation comprising porous silica nanoparticles and at least one pesticide, wherein the pesticide is entrapped within pores of the silica nanoparticles and the formulation has pesticide loading of at least 0.5% (w/w).
  • Such formulation(s) is a nanocomposite.
  • the pesticide is selected from one or more fungicide, insecticide, herbicide or a combination thereof.
  • a method of preparing a crop protection formulation comprising dispersing at least one pesticide in an aqueous solution of sodium silicate to obtain a precursor solution; adding sulfuric acid- surfactant mixture to the precursor solution to obtain porous silica nanoparticles entrapping at least one pesticide within its pores; and separating porous silica nanoparticles entrapping at least one pesticide within its pores, from the solution obtained in the previous step.
  • sulfuric acid-surfactant mixture comprises a surfactant selected from lignin, gelatin, octylamine, chitosan, dioctyl sulfosuccinate sodium salt (AOT) and combinations thereof.
  • a surfactant selected from lignin, gelatin, octylamine, chitosan, dioctyl sulfosuccinate sodium salt (AOT) and combinations thereof.
  • Such method(s), wherein the separation of porous silica nanoparticles entrapping at least one pesticide within its pores is carried out by centrifugation or filtration.
  • the present disclosure provides a cost effective and an efficient crop protection formulation comprising porous silica nanoparticles and at least one pesticide entrapped within its porous structure.
  • the crop protection formulation is a nanocomposite. Due to its nano-sized dimensions, the crop protection formulation are absorbed better by the plant tissues and thus provide improved crop protection against pests without the need of frequent re-applications. This reduces the environmental pollution and economical load on farmers.
  • the disclosed crop protection formulation includes a combination of pesticides entrapped within the pores of the silica nanoparticles. Such combination of pesticides prevents or delays development of resistance to pesticides among pests.
  • the present disclosure also provides a method of preparing said crop protection formulation.
  • the method is easy to perform and economical.

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  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Agronomy & Crop Science (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Toxicology (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne une formulation de protection des cultures. La formulation de protection des cultures comprend des nanoparticules de silice poreuse et au moins un pesticide, ledit pesticide étant piégé dans les pores des nanoparticules de silice et la formulation ayant une charge pesticide d'au moins 0,5 % (poids/poids). L'invention concerne un procédé de préparation de ladite formulation de protection des cultures.
PCT/IB2016/056895 2015-11-20 2016-11-16 Formulation de protection des cultures et procédé de préparation associé Ceased WO2017085636A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
IN4370/MUM/2015 2015-11-20
IN4370MU2015 2015-11-20

Publications (1)

Publication Number Publication Date
WO2017085636A1 true WO2017085636A1 (fr) 2017-05-26

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN113575243A (zh) * 2021-07-27 2021-11-02 中国热带农业科学院南亚热带作物研究所 一种液体水果套袋材料、其制备方法及应用
US20220202009A1 (en) * 2019-04-17 2022-06-30 Adolphe Merkle Institute, University Of Fribourg Method of production of controlled release silica nanoparticles for plant growth and/or defense enhancement
US11805773B1 (en) 2023-06-17 2023-11-07 King Faisal University Nanocomposite including water-soluble nano-polymer and mesoporous silica nanoparticles encapsulated with azole derivatives

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1695446A (zh) * 2004-05-14 2005-11-16 北京化工大学 一种农药组合物及其制备方法
US20120064140A1 (en) * 2009-05-12 2012-03-15 Wuxi Now Materials Corp. Composite nanogranules from polymer/inorganic nanoparticles, preparation method thereof and use of the same

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1695446A (zh) * 2004-05-14 2005-11-16 北京化工大学 一种农药组合物及其制备方法
US20120064140A1 (en) * 2009-05-12 2012-03-15 Wuxi Now Materials Corp. Composite nanogranules from polymer/inorganic nanoparticles, preparation method thereof and use of the same

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20220202009A1 (en) * 2019-04-17 2022-06-30 Adolphe Merkle Institute, University Of Fribourg Method of production of controlled release silica nanoparticles for plant growth and/or defense enhancement
US12433292B2 (en) * 2019-04-17 2025-10-07 Adolphe Merkle Institute, University Of Fribourg Method of production of controlled release silica nanoparticles for plant growth and/or defense enhancement
CN113575243A (zh) * 2021-07-27 2021-11-02 中国热带农业科学院南亚热带作物研究所 一种液体水果套袋材料、其制备方法及应用
CN113575243B (zh) * 2021-07-27 2022-10-04 中国热带农业科学院南亚热带作物研究所 一种液体水果套袋材料、其制备方法及应用
US11805773B1 (en) 2023-06-17 2023-11-07 King Faisal University Nanocomposite including water-soluble nano-polymer and mesoporous silica nanoparticles encapsulated with azole derivatives

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