WO1995002962A1 - Procede de production de concentres d'azadirachtine a partir de substances des graines du margousier a feuilles de frene - Google Patents

Procede de production de concentres d'azadirachtine a partir de substances des graines du margousier a feuilles de frene Download PDF

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Publication number
WO1995002962A1
WO1995002962A1 PCT/US1994/008298 US9408298W WO9502962A1 WO 1995002962 A1 WO1995002962 A1 WO 1995002962A1 US 9408298 W US9408298 W US 9408298W WO 9502962 A1 WO9502962 A1 WO 9502962A1
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WIPO (PCT)
Prior art keywords
azadirachtin
oil
polar solvent
group
mixtures
Prior art date
Application number
PCT/US1994/008298
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English (en)
Inventor
Kadambar S. Holla
Original Assignee
Agridyne Technologies, Inc.
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Agridyne Technologies, Inc. filed Critical Agridyne Technologies, Inc.
Priority to AU74031/94A priority Critical patent/AU7403194A/en
Publication of WO1995002962A1 publication Critical patent/WO1995002962A1/fr

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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
    • A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
    • A01N65/08—Magnoliopsida [dicotyledons]
    • A01N65/26—Meliaceae [Chinaberry or Mahogany family], e.g. mahogany, langsat or neem
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system

Definitions

  • This invention relates to a method for obtaining azadirachtinconcentrates fromazadirachtin-containingmaterials. More particularly, this invention relates to a method for producing an azadirachtin concentrate by extracting azadirachtin- containing oils from plant materials and precipitating the azadirachtin from the oils using a non-polar solvent.
  • Extracts of the neem tree (Azadirachta indica) , the chinaberry tree (Melia azedarach) , and other plants in the family Meliaceae (e.g. Azadirachta excelsa) have long been known to have insectici al activity (Natural Pesticides from the Neem Tree, Proc. 1st Int'l Neem Conf. 1980 [H. Schmutterer et al. eds. 1982]; Natural Pesticides from the Neem Tree and Other Tropical Plants, Proc. 2nd Int'l Neem Conf. 1983 [H. Schmutterer and K.R.S. Asher eds.
  • Azadirachtin a major active ingredient in many of these extracts, is a limonoid of the tetranortriterpenoid type. Azadirachtin has been shown to be a potent insect growth regulator and feeding deterrent with value as an active ingredient in commercial insecticides (R.B. Yamasaki et al. (1987) J. Agric. Food Che . 3_5:467-471) .
  • azadirachtin in commercial insecticides requires that the compound be extracted from the plant material and concentrated in a convenient form. Suitable azadirachtin concentrates are solid in form, have high levels of azadirachtin
  • 4,556,562 discloses a similar method whereby neem seeds are first reduced in size to that of a regular grind of coffee. Azadirachtin is then extracted at elevated temperatures, again using ethanol. No further concentration steps are used, however, and the final extract is a liquid containing only 0.5-1% azadirachtin.
  • Walter U.S. Patent No. 4,946,681 describes a related process for extracting azadirachtin from ground de-oiled neem seeds with aprotic solvents or alcohols. The liquid extract is further treated with molecular sieves to remove water. Carter et al. (U.S. Patent No.
  • 5,001,146 describes a two-step extraction process comprising a "cleanup" extraction with a non- polar aprotic solvent to remove the neem oil from the seeds, followed by a second extraction of the defatted neem seeds using a more polar, azadirachtin-soluble solvent.
  • the final extract from this process is a solution containing about 4.5 g/1 azadirachtin.
  • Kleeberg also describes a multi-step procedure whereby the azadirachtin is first extracted from neem oil and plant material using water. The aqueous fraction is then extracted with an organic solvent to remove the azadirachtin from the water.
  • a solid azadirachtin concentrate is ultimately obtained using a slow and inefficient phase separation followed by concentration of the organic phase and crystallization.
  • the present invention solves these problems by employing a simple and efficient precipitation step that produces an azadirachtin concentrate which is easily and efficiently separated from plant oils and other non-polar plant components.
  • the present invention thus represents a significant improvement over the pr or art methods.
  • the present invention rovides a practical and efficient process for producing an azadirachtin concentrate from azadirachtin-containing materials.
  • the process in accordance with the invention, is carried out by preparing an azadirachtin- containing plant oil and/or plant extract, then precipitating the azadirachtin and other polar compounds from the oil and/or extract with a non-polar solvent in which azadirachtin has low solubility.
  • Another principal object of the invention is to provide a method for recovering azadirachtin in a concentrated solid form rather than in a dilute solution.
  • the azadirachtin concentrate produced according to the instant method can be readily collected and separated from the liquid fraction ⁇ of the plant oil or extract.
  • Yet another object of the invention is its effectiveness in producing an azadirachtin-containing precipitate which can be readily separated from plant oils and other non-polar components of crude plant extracts.
  • Azadirachtin concentrates produced in accordance with the invention can be readily collected, dried and further processed. These concentrates have high levels of azadirachtin relative to the initial seed content. Such concentrates are convenient for storage and distribution purposes and are particularly suitable starting materials for azadirachtin-based products.
  • the invention relates to a method for extracting azadirachtin from azadirachtin-containing plant materials.
  • the invention is characterized by first obtaining azadirachtin- containing oils from said plant materials, preferably neem or chinaberry tree seeds, then precipitating the azadirachtin from the oils.
  • the oil-producing step can be accomplished by mechanical and/or chemical means, i.e., using oil expelling equipment and/or solvent extraction, respectively.
  • the azadirachtin is then precipitated from the expelled or extracted oil using a non-polar solvent in which azadirachtin has low solubility.
  • non-polar solvents in which azadirachtin has low solubility generally refers to non-polar solvents in which azadirachtin is less soluble than in mechanically expelled or chemically extracted neem oil.
  • expelled oil and mechanically expelled oil refer to oils that are removed from plant material using mechanical expelling techniques. Mechanical expelling in accordance with the present invention produces “expelled oil” and "expeller cake”.
  • extracted oil refers to oil- bearing extracts that are removed from plant materials using solvent extraction techniques.
  • Plant oil and neem oil generally refer to oils that are removed from plant materials and neem materials, respectively, using mechanical and/or solvent extraction techniques.
  • azadirachtin-containing precipitate As used herein, "azadirachtin-containing precipitate,” “azadirachtin-containing concentrate,” and “azadirachtin concentrate” refer to azadirachtin extracts comprising at least a ten-fold increase in percentage by weight of azadirachtin relative to the percentage by weight of azadirachtin in the plant material from which it is derived. Azadirachtin concentrates derived from neem seed kernel typically contain greater than 1-3% azadirachtin.
  • the azadirachtin concentrate produced by the present invention is obtained by extracting azadirachtin-containing oil from plant material by mechanical and/or chemical means, then precipitating the azadirachtin from the oil(s).
  • the process comprises the following steps:
  • the neem seeds are preferably dried and separated from unwanted debris, typically using vibrating screen shakers.
  • the seed kernels are then released from the cleaned seeds, for example using a "roller cracker” or “knife blade” sheller, and separated from hull materials, again using vibrating screen shakers or similar devices.
  • Cleaned neem seed kernels typically contain approximately 30-40% neem oil and 0.1-0.3% azadirachtin.
  • the step of producing oil from seed and/or kernel can be accomplished by either of two general procedures (mechanical or chemical) , or a combination thereof.
  • a first embodiment of this invention is to extract azadirachtin-containing plant oil from plant materials, such as the neem seed kernel exemplified herein, using mechanical expelling techniques.
  • the neem seed kernel fraction, prepared as described above, may be steamed or boiled to facilitate oil expelling.
  • Mechanical expelling techniques are well known in the art. They include, but are not limited to, grinding, flaking or pressing. The equipment used in the expelling step is not critical, and most traditional oil expelling machinery that grinds, flakes and/or presses the seeds or kernels to provide an acceptable yield of oil is suitable.
  • the expelling step generates liquid plant oil and solid expeller cake.
  • the oil carries a portion of the azadirachtin in solution.
  • the expelled oil is preferably filtered to remove particulate matter using, for example, a plate and frame filter, centrifuge, or the like. If desired, the filtered particulate matter and/or the expeller cake can be passed through the expeller again to optimize yield.
  • the expeller cake and/or the filtered particulate matter can also be chemically processed, as described below.
  • a second embodiment of this invention is to chemically extract azadirachtin and plant oil together from the plant material by mixing said plant material with a polar solvent.
  • the seed or kernel material is prepared as previously described. Preferably, it is also fractured or comminuted prior to extraction to improve extraction efficiency.
  • the expeller cake produced during the mechanical expelling step can be further treated with a polar solvent to remove residual oil and azadirachtin.
  • Solvent extraction may be carried out as a batch process by admixing seed kernel or expeller cake with a suitable polar solvent until an acceptable amount of azadirachtin and oil is removed.
  • the polar solvent extraction can be repeated to optimize extraction efficiency.
  • Solvent extraction can also be carried out as a continuous process, preferably in a fluid bed solvent extractor, again using a polar solvent.
  • efficiency of extraction can be enhanced by manipulating the extraction conditions, particularly the operating temperature and extraction time.
  • Solvent extraction is preferably carried out using ethylene dichloride or dichloromethane, which extract both azadirachtin and oil from plant material or expeller cake.
  • solvents may also be used with good results. Any solvent or combination of solvents which solubilizes or suspends azadirachtin and plant oil without causing the decomposition of azadirachtin is suitable.
  • Suitable solvents for use in this invention include, but are not limited to, ketones, alcohols, esters, ethers, nitriles, amides, sulfoxides, substituted aliphatic hydrocarbons, aromatic hydrocarbons and substituted aromatic hydrocarbons, and mixtures thereof.
  • Techniques are available to reduce the concentration of polar solvent in the extracted oil mixture to acceptable levels prior to the final processing steps. Techniques include, but are not limited to, passage through solvent strippers.
  • the low solvent level is generally accomplished by adjusting the number of stripper columns and/or the operating temperature and pressure (vacuum) of the columns.
  • the oil produced by mechanical expelling and/or solvent extraction techniques as described in the above embodiments is subsequently treated with a sufficient amount of a non-polar solvent to precipitate an azadirachtin concentrate.
  • the precipitation is generally accomplished by combining the expelled oil and/or extracted oils with a non-polar solvent and agitating the mixture in a vessel.
  • the oil and other non-polar components remain in solution, while the more polar components, including azadirachtin, precipitate in solid form.
  • Azadirachtin precipitation is carried out using a non-polar solvent in which azadirachtin has low solubility.
  • Any non-polar solvent or combination of solvents which precipitates azadirachtin is suitable.
  • Preferred solvents are straight- chained, branched or cyclic derivatives of pentanes, hexanes, heptanes, octanes, nonanes and decanes, and mixtures thereof. Paraffin oils and aromatic hydrocarbons, including mixtures thereof, are also preferred.
  • the solvents are hexanes, heptanes, and/or petroleum ethers. These solvents are relatively inexpensive and readily available. Comparative studies were performed to test the effects of experimental conditions on azadirachtin yield.
  • the examples show that various process parameters can be adjusted, if desired, to optimize precipitation efficiency. Specifically, the ratio of oil to solvent, the operating temperature and the addition rate of the reactants can be adjusted to maximize the yield of azadirachtin and/or the cost efficiency of the process. Although the procedure is effective over a broad range of temperatures, the preferred operating temperatures are within the range of 20-60° C. The treatment is independent of the order of addition of the reactants.
  • the precipitate is preferably dried by appropriate means to remove excess solvent.
  • This dried precipitate typically contains between 5% and 30% azadirachtin by weight.
  • Neem oil (0.125% azadirachtin) was obtained from cleaned, shelled neem seeds by mechanical expelling. The oil was then warmed to 50°C to dissolve all solids. Azadirachtin precipitation was carried out using 40 g aliquots of warmed neem oil, added over a two-minute period to an agitated vessel containing hexanes. The resulting precipitate was stirred in solvent for an additional 20 minutes, collected by filtration, washed with fresh hexanes, and air dried. The analysis of azadirachtin content in the precipitate was determined by HPLC using an external, analytically pure azadirachtin standard as described in, for instance: Uebel, E.C., et al.
  • Example 2 The same procedures were followed as in Example 1 above except that approximately 183 g of neem oil (0.125% azadirachtin) was added to 800 ml of hexanes, and the time over which the oil was added to the hexanes was varied from 3 to 2020 seconds. Results are shown in Table 2.
  • Example 3 The same procedures as in Example 1 were followed except that oil addition time was 4 minutes; the amounts of reagents were 182 g neem oil and 800 ml hexanes; and hexane temperature was varied from 1°C to 40° C. The calculated weight of azadirachtin in each oil sample was 0.228 g. Results are shown in Table 3.
  • a 1.1 kg sample of expelled neem cake was extracted in a Soxhlet extractor with 4 liters of ethylene dichloride at reflux for 18 hours to remove residual neem oil and azadirachtin.
  • the solution was filtered, the solvent was removed under vacuum, and the oil (260 ml) was assayed for azadirachtin content as described in Example 1.
  • the extracted oil contained 0.31% azadirachtin.
  • Solvent-extracted neem oil (113 g) prepared according to Example 5 was warmed to 50° C, transferred to an addition funnel, and added over a period of about four minutes to a magnetically stirred flask of hexanes at 25° C. The precipitated material was stirred an additional 20 minutes, then filtered, air dried, and analyzed for azadirachtin content as described in Example 1. Table 5 shows the effect of variation in oil-to-hexane ratio on precipitation of solvent-extracted neem oil. Table 5
  • Solvent-extracted neem oil (113 g) prepared according to Example 5 was warmed to 50° C and added over a four-minute period to an agitated vessel containing hexanes at the temperatures listed below. The final oil-to-solvent ratio in each case was 1:3. Table 6 illustrates the effect of solvent temperature on azadirachtin yield.
  • Example 8 Azadirachtin Precipitation using Mechanically Expelled Neem Oil.
  • One metric ton of decorticated neem seed kernel was processed using a commercial oil expeller to remove approximately 80% of the neem oil.
  • the expelling step yielded approximately 300 kg of neem oil and approximately 700 kg of neem kernel cake.
  • the oil was slowly added to an agitated vessel containing 1200 liters of hexanes.
  • the polar materials in the oil, including azadirachtin precipitated out in solid form.
  • the solid precipitate was then collected by filtration and air dried.
  • the dried azadirachtin concentrate (1.8 kg) contained approximately 220 g (12%) azadirachtin.
  • Decorticated neem seed kernel 500 g was ground in a blender in the presence of ethyl acetate. The mixture of ground neem seed kernel and ethyl acetate was transferred to a flask containing two additional liters of ethyl acetate. The mixture was stirred for five hours at 60° C, then filtered through celite and sand. The filtrate was concentrated and added to one liter of stirred hexanes. The dried azadirachtin concentrate (5.83 g) was collected by filtration and found to contain 0.51 g (8.8%) azadirachtin.
  • Example 10 The Effect of Solvent Type on Azadirachtin Precipitation.

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  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Zoology (AREA)
  • Wood Science & Technology (AREA)
  • Agronomy & Crop Science (AREA)
  • Environmental Sciences (AREA)
  • Natural Medicines & Medicinal Plants (AREA)
  • Plant Pathology (AREA)
  • Dentistry (AREA)
  • Mycology (AREA)
  • Biotechnology (AREA)
  • Microbiology (AREA)
  • Pest Control & Pesticides (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicines Containing Plant Substances (AREA)
  • Extraction Or Liquid Replacement (AREA)

Abstract

Ce procédé permet de produire un concentré d'azadirachtine par extraction dans des substances végétales des huiles contenant de l'azadirachtine, et en faisant un précipité d'azadirachtine dans des huiles utilisant un solvant non polaire dans lequel l'azadirachtine a une faible solubilité.
PCT/US1994/008298 1993-07-21 1994-07-21 Procede de production de concentres d'azadirachtine a partir de substances des graines du margousier a feuilles de frene WO1995002962A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU74031/94A AU7403194A (en) 1993-07-21 1994-07-21 Method for producing azadirachtin concentrates from neem seed materials

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US08/094,779 1993-07-21
US08/094,779 USH1541H (en) 1993-07-21 1993-07-21 Method for producing azadirachtin concentrates from neem seed materials

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0789513A1 (fr) * 1995-06-07 1997-08-20 Thermo Trilogy Corporation Stabilite amelioree d'un solide contenant de l'azadirachtine
EP0834254A1 (fr) * 1996-10-02 1998-04-08 Council of Scientific and Industrial Research Formulations de l'azadirachtine et leur préparation à partir des graines de l'arbre neem
AU718833B2 (en) * 1995-10-19 2000-04-20 Council Of Scientific And Industrial Research Pesticidal dry powder formulation
WO2021222814A1 (fr) 2020-05-01 2021-11-04 Vestaron Corporation Combinaisons insecticides

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6193974B1 (en) * 1995-07-17 2001-02-27 Dalmia Center For Research And Development Process of preparing purified azadirachtin in powder form from neem seeds and storage stable aqueous composition containing azadirachtin
IN179008B (fr) * 1995-07-17 1997-08-09 Dalmia Ct For Biotechnology
US5824291A (en) * 1997-06-30 1998-10-20 Media Group Chewing gum containing a teeth whitening agent
AUPO786197A0 (en) * 1997-07-11 1997-08-07 Neem Extracts Pty Ltd Azadirachtin extraction process
EP0930073B1 (fr) * 1998-01-14 2004-08-04 National Research Development Corporation of India Procédé de préparation d'un agent spermicide
US6866856B2 (en) 2002-12-31 2005-03-15 Avon Products, Inc. Compositions and delivery methods for the treatment of wrinkles, fine lines and hyperhidrosis
DE102005026424A1 (de) * 2005-06-08 2006-12-14 Terra Nostra Produkte Mit Naturextrakten Gmbh Verfahren zur Herstellung eines Margosaextraktes
BR102013021210B1 (pt) * 2013-01-25 2015-12-01 Fundação Universidade Fed De São Carlos processo de obtenção de nanopartículas biopoliméricas contendo óleo e extratos de azadirachta indica a. juss (neem), nanopartículas biopoliméricas e micropartículas em pó

Citations (4)

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Publication number Priority date Publication date Assignee Title
US4556562A (en) * 1984-03-19 1985-12-03 Vikwood, Ltd. Stable anti-pest neem seed extract
US4946681A (en) * 1989-06-26 1990-08-07 W. R. Grace & Co.-Conn. Method to prepare an improved storage stable neem seed extract
US5001146A (en) * 1989-06-26 1991-03-19 W. R. Grace & Co.-Conn. Storage stable azadirachtin formulation
WO1992016109A1 (fr) * 1991-03-22 1992-10-01 Trifolio-M Gmbh, Herstellung Und Vertrieb Hochreiner Biosubstanzen Procede pour la fabrication d'un insecticide riche en azadirachtine, supportant le stockage, a base de graines de l'arbre neem

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4556562A (en) * 1984-03-19 1985-12-03 Vikwood, Ltd. Stable anti-pest neem seed extract
US4946681A (en) * 1989-06-26 1990-08-07 W. R. Grace & Co.-Conn. Method to prepare an improved storage stable neem seed extract
US5001146A (en) * 1989-06-26 1991-03-19 W. R. Grace & Co.-Conn. Storage stable azadirachtin formulation
US5124349A (en) * 1989-06-26 1992-06-23 W. R. Grace & Co.-Conn. Storage stable azadirachtin formulation
US5124349B1 (en) * 1989-06-26 1998-10-20 Grace W R & Co Storage stable azadirachtin formulation
WO1992016109A1 (fr) * 1991-03-22 1992-10-01 Trifolio-M Gmbh, Herstellung Und Vertrieb Hochreiner Biosubstanzen Procede pour la fabrication d'un insecticide riche en azadirachtine, supportant le stockage, a base de graines de l'arbre neem

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
JOURNAL OF NATURAL PRODUCTS, Volume 50, Number 2, issued April 1987, SCHROEDER et al., "A Simplified Isolation Procedure for Azadirachtin", pages 241-244. *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0789513A1 (fr) * 1995-06-07 1997-08-20 Thermo Trilogy Corporation Stabilite amelioree d'un solide contenant de l'azadirachtine
EP0789513A4 (fr) * 1995-06-07 1999-06-16 Thermo Trilogy Corp Stabilite amelioree d'un solide contenant de l'azadirachtine
AU718833B2 (en) * 1995-10-19 2000-04-20 Council Of Scientific And Industrial Research Pesticidal dry powder formulation
EP0834254A1 (fr) * 1996-10-02 1998-04-08 Council of Scientific and Industrial Research Formulations de l'azadirachtine et leur préparation à partir des graines de l'arbre neem
WO2021222814A1 (fr) 2020-05-01 2021-11-04 Vestaron Corporation Combinaisons insecticides

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AU7403194A (en) 1995-02-20

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