WO2013135915A1 - Uso de aceites esenciales, extractos supercríticos y residuos acuosos generados en un proceso de obtención de extractos orgánicos de la planta artemisia absinthium l - Google Patents
Uso de aceites esenciales, extractos supercríticos y residuos acuosos generados en un proceso de obtención de extractos orgánicos de la planta artemisia absinthium l Download PDFInfo
- Publication number
- WO2013135915A1 WO2013135915A1 PCT/ES2012/070162 ES2012070162W WO2013135915A1 WO 2013135915 A1 WO2013135915 A1 WO 2013135915A1 ES 2012070162 W ES2012070162 W ES 2012070162W WO 2013135915 A1 WO2013135915 A1 WO 2013135915A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- organic
- essential oil
- nematodes
- aqueous residue
- natural
- Prior art date
Links
- 239000000284 extract Substances 0.000 title claims abstract description 79
- 238000000034 method Methods 0.000 title claims abstract description 64
- 239000000341 volatile oil Substances 0.000 title claims abstract description 59
- 240000002877 Artemisia absinthium Species 0.000 title claims abstract description 44
- 230000008569 process Effects 0.000 title description 24
- 238000000605 extraction Methods 0.000 claims abstract description 41
- 241000196324 Embryophyta Species 0.000 claims abstract description 40
- 230000003032 phytopathogenic effect Effects 0.000 claims abstract description 33
- 241000244206 Nematoda Species 0.000 claims abstract description 28
- 241000233866 Fungi Species 0.000 claims abstract description 16
- 239000000417 fungicide Substances 0.000 claims abstract description 13
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 61
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 40
- 235000003097 Artemisia absinthium Nutrition 0.000 claims description 28
- 239000012071 phase Substances 0.000 claims description 25
- 230000000855 fungicidal effect Effects 0.000 claims description 24
- 230000001069 nematicidal effect Effects 0.000 claims description 24
- 239000005645 nematicide Substances 0.000 claims description 21
- 238000004519 manufacturing process Methods 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 13
- 238000009472 formulation Methods 0.000 claims description 12
- IRZWAJHUWGZMMT-UHFFFAOYSA-N 4,6,6-trimethylbicyclo[3.1.1]hept-3-en-7-ol Chemical compound CC1=CCC2C(C)(C)C1C2O IRZWAJHUWGZMMT-UHFFFAOYSA-N 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 5
- 238000009329 organic farming Methods 0.000 claims description 5
- 239000002689 soil Substances 0.000 claims description 5
- 230000012010 growth Effects 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 238000005507 spraying Methods 0.000 claims description 4
- 239000002699 waste material Substances 0.000 claims description 4
- 241000223221 Fusarium oxysporum Species 0.000 claims description 3
- 241000427940 Fusarium solani Species 0.000 claims description 3
- 241000233732 Fusarium verticillioides Species 0.000 claims description 3
- 241001143352 Meloidogyne Species 0.000 claims description 3
- 239000002671 adjuvant Substances 0.000 claims description 3
- 208000015181 infectious disease Diseases 0.000 claims description 3
- 230000002458 infectious effect Effects 0.000 claims description 3
- 230000000366 juvenile effect Effects 0.000 claims description 3
- 238000001179 sorption measurement Methods 0.000 claims description 3
- 239000008346 aqueous phase Substances 0.000 claims description 2
- 230000005764 inhibitory process Effects 0.000 claims description 2
- 239000002054 inoculum Substances 0.000 claims description 2
- 238000002414 normal-phase solid-phase extraction Methods 0.000 claims description 2
- 238000003756 stirring Methods 0.000 claims description 2
- BTHAWHOTHGQIKC-VURMDHGXSA-N (5z)-2,6-dimethylocta-5,7-diene-2,3-diol Chemical compound C=CC(/C)=C\CC(O)C(C)(C)O BTHAWHOTHGQIKC-VURMDHGXSA-N 0.000 abstract 1
- 235000003261 Artemisia vulgaris Nutrition 0.000 description 20
- 239000001138 artemisia absinthium Substances 0.000 description 18
- 239000000126 substance Substances 0.000 description 17
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 16
- 235000009051 Ambrosia paniculata var. peruviana Nutrition 0.000 description 15
- 235000017731 Artemisia dracunculus ssp. dracunculus Nutrition 0.000 description 15
- 239000003921 oil Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- 230000000694 effects Effects 0.000 description 9
- 239000002028 Biomass Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- 238000004821 distillation Methods 0.000 description 6
- 235000003826 Artemisia Nutrition 0.000 description 5
- 244000030166 artemisia Species 0.000 description 5
- 235000009052 artemisia Nutrition 0.000 description 5
- 230000008901 benefit Effects 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000008131 herbal destillate Substances 0.000 description 4
- 230000017260 vegetative to reproductive phase transition of meristem Effects 0.000 description 4
- 241000238876 Acari Species 0.000 description 3
- 235000013323 absinthe Nutrition 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 238000003306 harvesting Methods 0.000 description 3
- 229930003658 monoterpene Natural products 0.000 description 3
- 150000002773 monoterpene derivatives Chemical class 0.000 description 3
- 235000002577 monoterpenes Nutrition 0.000 description 3
- 239000005871 repellent Substances 0.000 description 3
- 230000002940 repellent Effects 0.000 description 3
- 241000894007 species Species 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OPFTUNCRGUEPRZ-QLFBSQMISA-N (-)-beta-elemene Chemical compound CC(=C)[C@@H]1CC[C@@](C)(C=C)[C@H](C(C)=C)C1 OPFTUNCRGUEPRZ-QLFBSQMISA-N 0.000 description 2
- 241001124076 Aphididae Species 0.000 description 2
- 241000255925 Diptera Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- WEEGYLXZBRQIMU-UHFFFAOYSA-N Eucalyptol Chemical compound C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 description 2
- 241000237858 Gastropoda Species 0.000 description 2
- 241000238631 Hexapoda Species 0.000 description 2
- 241000258916 Leptinotarsa decemlineata Species 0.000 description 2
- 241000243785 Meloidogyne javanica Species 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 2
- 238000004166 bioassay Methods 0.000 description 2
- 230000002728 bioinsecticidal effect Effects 0.000 description 2
- 238000007906 compression Methods 0.000 description 2
- 230000006835 compression Effects 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- 238000005520 cutting process Methods 0.000 description 2
- 238000010586 diagram Methods 0.000 description 2
- 238000004817 gas chromatography Methods 0.000 description 2
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 2
- 230000009036 growth inhibition Effects 0.000 description 2
- 230000001524 infective effect Effects 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 2
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 229930014626 natural product Natural products 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 239000002304 perfume Substances 0.000 description 2
- 239000011148 porous material Substances 0.000 description 2
- 239000010909 process residue Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- -1 waxes Chemical class 0.000 description 2
- NPNUFJAVOOONJE-ZIAGYGMSSA-N β-(E)-Caryophyllene Chemical compound C1CC(C)=CCCC(=C)[C@H]2CC(C)(C)[C@@H]21 NPNUFJAVOOONJE-ZIAGYGMSSA-N 0.000 description 2
- OPFTUNCRGUEPRZ-UHFFFAOYSA-N (+)-beta-Elemen Natural products CC(=C)C1CCC(C)(C=C)C(C(C)=C)C1 OPFTUNCRGUEPRZ-UHFFFAOYSA-N 0.000 description 1
- WTARULDDTDQWMU-RKDXNWHRSA-N (+)-β-pinene Chemical compound C1[C@H]2C(C)(C)[C@@H]1CCC2=C WTARULDDTDQWMU-RKDXNWHRSA-N 0.000 description 1
- WTARULDDTDQWMU-IUCAKERBSA-N (-)-Nopinene Natural products C1[C@@H]2C(C)(C)[C@H]1CCC2=C WTARULDDTDQWMU-IUCAKERBSA-N 0.000 description 1
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 1
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 1
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 240000005925 Aeschynanthus radicans Species 0.000 description 1
- 241000223600 Alternaria Species 0.000 description 1
- 241000223602 Alternaria alternata Species 0.000 description 1
- 206010002368 Anger Diseases 0.000 description 1
- 241000208838 Asteraceae Species 0.000 description 1
- 241000123650 Botrytis cinerea Species 0.000 description 1
- 244000056139 Brassica cretica Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- 244000223760 Cinnamomum zeylanicum Species 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 241001465977 Coccoidea Species 0.000 description 1
- 241000254173 Coleoptera Species 0.000 description 1
- 241000254171 Curculionidae Species 0.000 description 1
- 241000275449 Diplectrum formosum Species 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- 241001149959 Fusarium sp. Species 0.000 description 1
- 240000005979 Hordeum vulgare Species 0.000 description 1
- 241000257303 Hymenoptera Species 0.000 description 1
- 241000255777 Lepidoptera Species 0.000 description 1
- 244000237986 Melia azadirachta Species 0.000 description 1
- 235000013500 Melia azadirachta Nutrition 0.000 description 1
- 241000243786 Meloidogyne incognita Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 240000001766 Mycetia javanica Species 0.000 description 1
- HIGQPQRQIQDZMP-DHZHZOJOSA-N Neryl acetate Natural products CC(C)=CCC\C(C)=C\COC(C)=O HIGQPQRQIQDZMP-DHZHZOJOSA-N 0.000 description 1
- 239000008896 Opium Substances 0.000 description 1
- 241000488583 Panonychus ulmi Species 0.000 description 1
- 206010034133 Pathogen resistance Diseases 0.000 description 1
- 241001325166 Phacelia congesta Species 0.000 description 1
- 241000255969 Pieris brassicae Species 0.000 description 1
- WTARULDDTDQWMU-UHFFFAOYSA-N Pseudopinene Natural products C1C2C(C)(C)C1CCC2=C WTARULDDTDQWMU-UHFFFAOYSA-N 0.000 description 1
- 235000003434 Sesamum indicum Nutrition 0.000 description 1
- 244000040738 Sesamum orientale Species 0.000 description 1
- 241000258242 Siphonaptera Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 241000256250 Spodoptera littoralis Species 0.000 description 1
- 235000007303 Thymus vulgaris Nutrition 0.000 description 1
- 240000002657 Thymus vulgaris Species 0.000 description 1
- 244000157222 Thymus zygis Species 0.000 description 1
- 235000017826 Thymus zygis Nutrition 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000002814 agar dilution Methods 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 230000009418 agronomic effect Effects 0.000 description 1
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 1
- 229940126675 alternative medicines Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000507 anthelmentic effect Effects 0.000 description 1
- 230000001887 anti-feedant effect Effects 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000000729 antidote Substances 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 230000003078 antioxidant effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 230000036528 appetite Effects 0.000 description 1
- 235000019789 appetite Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- NPNUFJAVOOONJE-UHFFFAOYSA-N beta-cariophyllene Natural products C1CC(C)=CCCC(=C)C2CC(C)(C)C21 NPNUFJAVOOONJE-UHFFFAOYSA-N 0.000 description 1
- UAHWPYUMFXYFJY-UHFFFAOYSA-N beta-myrcene Chemical compound CC(C)=CCCC(=C)C=C UAHWPYUMFXYFJY-UHFFFAOYSA-N 0.000 description 1
- 229930006722 beta-pinene Natural products 0.000 description 1
- 210000000941 bile Anatomy 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 230000000853 biopesticidal effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 239000003874 central nervous system depressant Substances 0.000 description 1
- 235000017803 cinnamon Nutrition 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- 238000012272 crop production Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 230000001079 digestive effect Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000000686 essence Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 210000000232 gallbladder Anatomy 0.000 description 1
- LCWMKIHBLJLORW-UHFFFAOYSA-N gamma-carene Natural products C1CC(=C)CC2C(C)(C)C21 LCWMKIHBLJLORW-UHFFFAOYSA-N 0.000 description 1
- 210000004051 gastric juice Anatomy 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- HIGQPQRQIQDZMP-UHFFFAOYSA-N geranil acetate Natural products CC(C)=CCCC(C)=CCOC(C)=O HIGQPQRQIQDZMP-UHFFFAOYSA-N 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 210000004209 hair Anatomy 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 235000001510 limonene Nutrition 0.000 description 1
- 229940087305 limonene Drugs 0.000 description 1
- 229930007744 linalool Natural products 0.000 description 1
- 238000000622 liquid--liquid extraction Methods 0.000 description 1
- 238000002803 maceration Methods 0.000 description 1
- 239000002207 metabolite Substances 0.000 description 1
- 239000003094 microcapsule Substances 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 239000006272 natural pesticide Substances 0.000 description 1
- HIGQPQRQIQDZMP-FLIBITNWSA-N neryl acetate Chemical compound CC(C)=CCC\C(C)=C/COC(C)=O HIGQPQRQIQDZMP-FLIBITNWSA-N 0.000 description 1
- 229960001027 opium Drugs 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000002786 root growth Effects 0.000 description 1
- 229930000044 secondary metabolite Natural products 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 229930004725 sesquiterpene Natural products 0.000 description 1
- 150000004354 sesquiterpene derivatives Chemical class 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 230000028070 sporulation Effects 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000000194 supercritical-fluid extraction Methods 0.000 description 1
- 239000011885 synergistic combination Substances 0.000 description 1
- 239000006273 synthetic pesticide Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000001585 thymus vulgaris Substances 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 235000020047 vermouth Nutrition 0.000 description 1
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]
- A01N65/12—Asteraceae or Compositae [Aster or Sunflower family], e.g. daisy, pyrethrum, artichoke, lettuce, sunflower, wormwood or tarragon
-
- 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
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/04—Oxygen or sulfur attached to an aliphatic side-chain of a carbocyclic ring system
-
- 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
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/06—Oxygen or sulfur directly attached to a cycloaliphatic ring system
-
- 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
Definitions
- the present specification refers to a procedure for the extraction of organic derivatives from the Artemisia Absinthium L. r plant commonly known as Wormwood, and more specifically to the application of said extracts as a fungicidal active compound against phytopathogenic fungi and to the application of residues generated in the procedure as nematicides against phytopathogenic nematodes.
- the invention is based on the organic production of the specific chemotype plant in order to produce organic extracts by steam entrainment (essential oils), supercritical extracts with CO 2 and collect the aqueous residue from the extraction of the essential oil (hydrolate), considered in the agricultural sector as a waste without value.
- the invention encompasses in a general way within the field of industrial chemistry, in what refers to the process of obtaining organic extracts derived from Artemisia absinthium L (wormwood), and more particularly within the field of Agriculture, being the most important application of these compounds and of the residues that are generated in their process that of fungicide and nematicide, respectively. Because they are natural substances, they have great value in organic farming, that is, where synthetic chemicals are not used.
- Artemisia absinthuim L. r commonly referred to as "wormwood” is a medicinal herbaceous plant of the Asteraceae family. Every year it produces straight branches from its base, from 0.50 to 1.20 m high, which are dried in autumn after fruiting. The basal parts of these branches remain during the winter and in the following season new branches are produced from their buds. The whole plant has a whitish coloration, due to its abundance of hairs that cover practically the entire surface of stem and leaves. Its range covers mainly from Central Asia to Western Europe, with some locations in North Africa. It has been a very cultivated plant for its aromatic character, especially in the United States, the former USSR and France. The plant is collected when it is in full bloom, between July and August. The first year the collection is scarce, but in the following years it is possible to make two collections, in July and at the end of October, if the weather conditions allow it.
- Wormwood micropropagation methods have also been developed to produce plants in order to obtain secondary metabolites.
- Absinthe has also been used since ancient times for the treatment of digestive disorders since it stimulates appetite, prevents the formation of gases in the digestive tract, stimulates the secretion of gastric juices and bile both by the gallbladder and by the liver and protects against liver ailments. It also has antipyretic, antioxidant and anti-inflammatory properties. It has also been used as an antidote for opium and other poisons central nervous system depressants. It is also known applications in perfumes, as disclosed in international patent application WO0249600 Al ("Perfume compositions”), or as elements for use in alternative medicines, as for example described in Spanish patent ES 2076896 Bl ("Procedure to produce moxas").
- insecticidal and repellent properties are traditionally known, and frequently used, in the fight against pests, especially aphids, mites, mealybugs, ants, caterpillars, and other insects by spraying their extract on the affected plants. It also repels cabbage butterfly, mites, rust, snails and slugs, if sprayed preventively. It has been proven that the essential oil extracted from certain chemotypes of wormwood serves as an acaricide against the red spider and as an insecticide against weevils and common fly. It has also been used as a repellent for fleas, flies, mosquitoes, moths and ticks. On the other hand, the extract has also turned out to have toxic and anti-food effects against the potato beetle (Leptinotarse decemnlineata).
- the inventors of the present application have developed in the Spanish patent application P201031389 a procedure for the extraction of bioinsecticidal derivatives of the Artemisia Absinthium L. plant characterized in that it is defined by an organic extract extraction phase, obtaining essential oil and non-volatile extract, and a phase of extracting supercritical extracts with CO 2 , starting from a specific chemotype plant that is previously selected and cultivated.
- bioinsecticidal derivatives of the Artemisia Absinthium L plant are obtained, thus achieving optimum use of the extracts of said plant, with results reproducible and industrially applicable.
- the agronomic and economic parameters of organic production of the wormwood plant are established in experimental plots in order to produce organic extracts consisting of essential oil and non-volatile extract, and in another extraction phase extracts supercritical CO 2 chemical composition characterized with experimentally demonstrated repellent effects against larvae of Lepidoptera, for example of the species Spodoptera littoralis, aphids and Colorado potato beetle (Leptinotarsa decemlineata) in addition to having effects on root growth of barley Hordeum vulgare .
- a new industrial application of the essential oils and supercritical extracts extracted from the Artemisia Absinthium L. plant is tested by means of the aforementioned procedure as a fungicide for the control of the growth of phytopathogenic fungi that affect agricultural crops (not animals, such as it is already known for some chemotypes of this plant).
- a relevant aspect of the present invention is the application or use of aqueous residues or hydrolates that are generated in said process (and which are common by-products in this type of distillation of aromatic plants) as nematicides, against the attack of phytopathogenic nematodes in agricultural crops.
- the present invention relates firstly to the use of an essential oil and / or a supercritical extract extracted both from the Artemisia absinthium L. r population of Teruel and / or Sierra Nevada as a fungicide, that is, for the control of Phytopathogenic fungi in agricultural crops.
- This essential oil and this supercritical extract are obtained by means of an extraction procedure that comprises a production methodology phase of said plant, an extraction phase of organic extracts in which said essential oil is obtained and a non-volatile extract (of ethanolic nature ), and a phase of extraction by means of supercritical CO 2 .
- These extracts have a defined chemical composition.
- supercritical extract is understood as those fractions obtained by extracting the plant material with supercritical CO 2 at defined temperatures and temperatures.
- a second object of the invention is the aqueous residue (or hydrolate) generated in the extraction phase of the essential oil of the aforementioned process (and which is defined in Spanish patent application P201031389), and of its use as a nematicide, that is to say for the control of phytopathogenic nematodes in agricultural crops.
- said residue is specifically obtained from the essential oil extraction process of the Artemisia absinthium L. plant, Candial variety from Teruel and / or Sierra Nevada, said residue thus comprising an organic component containing in turn (Z) -2,6-dimethyllocta-5,7-diene-2,3-diol as an active organic compound against phytopathogenic nematodes.
- the chemical composition of the essential oil and the supercritical extract obtained from plants is generally characteristic of each species.
- the species Artemisia absinthium L Candial variety, populations of Teruel and Sierra Nevada is specifically used, which has allowed obtaining a specific essential oil that includes the intended uses. This Candial variety of the Artemisia absinthium L.
- the production methodology phase preferably includes the field cultivation of a chemotype selected from the plant in question for its adaptability to the crop and for its chemical composition, which as stated is the Candial variety, native to Teruel (Aragon) and Sierra Nevada (Granada), which is free of tuyonas.
- Said cultivation is preferably carried out by multiplication, more preferably by means of cuttings or seeds in nursery-seedbed for later planting in the seating area.
- This seating area is preferably located in high areas with rainfall greater than 400-450 mm per year, and is also preferably worked by mechanized cultivation.
- the crop goes into production in the first year of its plantation, and must then proceed to the collection of the biomass part of the plant that is used to perform the procedure for obtaining organic extracts, which preferably consists of the leaves and flowering tops when the plants are in the phenological stage of full flowering, and must subsequently proceed to the drying and grinding of the biomass collected.
- the drying is carried out in the shade, under air flow and for a period of approximately 8 days.
- the extraction phase of the organic extracts which is also when the aqueous residue or hydrolate is generated, is commonly carried out by hydrodestilation (by steam drag) and organic extraction of the collected material, thus obtaining the essential oil and a non-volatile extract, In addition to an aqueous by-product or hydrolate, which is a process residue.
- the extraction phase of supercritical extracts with CO 2 of determined chemical composition is preferably carried out using a compression pump with a filter, an extraction cylinder, two manifolds, a cylindrical cooling device, a heat exchanger, a pressure sensor and A flow meter.
- the collected material is introduced into the extraction cylinder and is symmetrically embedded with inert porous materials that allow a homogeneous flow of CO 2 , then heated until a temperature of 40 ° C is reached, then compressed the pump and CO 2 until a pressure of 90 bar is achieved, at which time the supercritical fluid at the working pressure fills the extraction cylinder, regulating the pressure in the two manifolds, using the appropriate valves, and the temperature through the device cooling, so that the first of the collectors serves to remove heavy compounds, such as waxes, and the second collector for the collection of the supercritical extract.
- the average particle size value of the collected size used is 0.5 mm, and the gas flow through the extractor cylinder at 25 ° C and 1 atm. It is 10.5 1 / min.
- FIG. 1 A preferred practical embodiment of the process in question is presented in Figure 1, with a simplified block diagram, to illustrate the process from which the products of interest in this invention are obtained.
- This procedure for the extraction of organic derivatives of wormwood provides multiple advantages over others available in the field of the art, such as contemplating a field crop production methodology, with specific chemotypes selected and through a controlled extraction of the raw material, enabling controlled, predictable and industrializable production. It also highlights the advantage of control at source that involves the chemical and biological standardization of the organic extracts obtained, as well as the optimization of the performance achieved thanks to the extraction with supercritical CO 2 .
- the essential oil obtained from the species A. absinthium consists of a more or less complex mixture of terpenic compounds, of low molecular weight.
- the interest of the specific essential oil obtained in the present invention for the intended use lies in the activity of its compounds.
- the essential oil of A. absinthium, Teruel (AAT) and Sierra Nevada (AASN) populations presents fundamentally terpenic components, belonging to various structural types, monoterpenes and sesquiterpenes that appear in varying amounts depending on the year of harvest of the plant.
- the extracted essential oil that is applied in the present invention as a fungicide comprises among its components: epoxyocimeno between 26-44% of the total composition, chrysanthenol between 12-30%, and monoterpene (Z) - 2,6-dimethyllocta-5, 7-diene-2,3-diol between 0.001% and 20%, and preferably appears in a maximum of 20% of the total composition.
- Table 1 Chemical composition of A. absinthium ndial variety, Teruel (AVAAT) and Sierra Nevada (AVAASN) populations
- Azulene 1.13 1.09 0.87 1, 11 Thanks to the chemical composition of the essential oil obtained from the process, it has utility as a fungicidal agent. Specifically, it has been found that extracts obtained preferably by hydrodestilation (by steam entrainment) in the described process (essential oils) are effective fungicides against phytopathogenic fungi, preferably against the species Alternar ⁇ a alternata, Fusarium oxysporum, F. moniliforme and F. solani, being even more effective against Botrytys cinnerea.
- the yield obtained from the essential oil varies in a range of 0.1-0.2% of the green biomass collected and used in the process.
- aqueous residue, or hydrolate generated in the process of extracting essential oils, it is a very effective nematicide against nodule-forming phytopathogenic nematodes (Meloidogyne sp.).
- its aqueous state facilitates the direct application of the hydrolate generated in the extraction on the crop to be treated, as a nematicidal formulation, without requiring any other component, which represents an added advantage for this residue that is now used as an elaborated product.
- the yield obtained from the hydrolate or aqueous residue in the described process varies in a range of 150-200 liters per 800-1000 kg of biomass collected and used in said process.
- Said aqueous residue is characterized by containing an active organic part against nematodes (also referred to herein as "organic component of the aqueous residue") which is mostly comprised of (Z) -2, 6-dimethyllocta-5, 7- has -2,3-diol of general formula (I), active organic component also present in the oil, but in a smaller amount (see Table 1).
- organic component of the aqueous residue also referred to herein as "organic component of the aqueous residue” which is mostly comprised of (Z) -2, 6-dimethyllocta-5, 7- has -2,3-diol of general formula (I), active organic component also present in the oil, but in a smaller amount (see Table 1).
- this aqueous or hydrolate residue contains a natural and active organic part that comes from the plant and is carried in the water used in the process of extracting the essential oil, water that is normally discarded as waste.
- the active organic part of the aqueous residue is usually obtained in a concentration range between 1 and 4 gr / 1 of aqueous residue.
- the aforementioned active compound (Z) -2,6-dimethyllocta-5,7-diene-2,3-diol) represents at least 80% of the total and never more than 90% (i.e. it is contained in a percentage between 80% and 90% of the total composition of the residue, including both limits), being responsible for the nematicidal activity of the aqueous residue.
- the decantation of the aqueous residue is performed by adding CINa to facilitate the process.
- the percentage of adsorption on activated carbon is 99% of the organic component of the residue (organic part) containing between 80% and 90% of the active organic component (Z) -2, 6-dimethyllocta-5, 7-diene -2,3-diol.
- this organic component or organic part of the residue in solid format is adsorbed on activated carbon.
- the present specification also refers to activated carbon obtained by the described method, and which contains the organic component extracted from the residue adsorbed on the carbon, as well as to the filtration cartridge manufactured from said carbon, taking into account that both can be used as a nematicide against phytopathogenic nematodes.
- the active component (Z) -2,6-dimethyllocta-5,7-diene-2,3-diol in the pure state can be obtained from the resulting activated carbon by extraction of the activated carbon.
- this extraction can be done through the use of solvents, it has been found that it is more advantageous to extract said carbon and separate it from the organic part of the residue with supercritical CO 2 , resulting in an organic extract enriched in the active and carbon-free component ; the content in the organic extract of the active component (Z) - 2,6,6-dimethyllocta-5,7-diene-2,3-diol varies between 80% and 100%, that is, its composition can be completely (Z) -2,6-dimethyllocta-5,7-diene-2,3-diol.
- This final enriched organic extract as well as the aqueous residue from which the organic part proceeds and said organic part extracted in solid format (adsorbed on activated carbon), can be used as a nematicidal agent of phytopathogenic nematodes.
- both of the activated carbon obtained by the above procedure and of the enriched organic extract itself can be for example by application of the product in the soil of the crop, with the same effects as the aqueous residue.
- An added advantage for this natural product is that in its manufacture active carbon is used, a cheap component that does not contaminate, or even commercialize it, without carbon.
- the main industrial applications of the essential oils and supercritical extracts obtained in the process consist in being the base material for preparing formulations of natural fungicides, of special application in agriculture and more especially in organic farming, as well as their use as an ingredient for mixed formulations, that is, for formulations that comprise synergistic combinations together with other natural active components with the same function (fungicide or nematicide, in each case).
- the hydrolate or aqueous residue in addition to being also used as the base material for natural nematicidal compositions, can be applied directly to the indicated concentrations on the crop to be treated.
- a third object of the present invention is a natural fungicidal composition, that is to say it contains excipients compatible with organic farming, which comprises at least the essential oil and / or the above-mentioned supercritical extract as an active component, normally (although not exclusively) together with at least one excipient and an adjuvant normally employed in the field of agriculture.
- the fungicidal composition further comprises at least one other active component other than oil.
- the fungicidal composition comprises an amount of essential oil and / or supercritical extract sufficient to reach 50% inhibition of fungus growth, amount equivalent to the effective dose of fungicidal action of the essential oil.
- Said effective dose varies depending on the fungus to be treated; Thus, it is 3 -5% compared to Fusarium sp. , 2% against A. alternata and 0.3% against Botrytis cinerea, of the total fungicidal composition that contains it.
- a fourth object of the present invention consists of a natural nematicidal composition
- a natural nematicidal composition comprising the aqueous residue or hydrolate, the organic part of said aqueous residue, or the organic extract rich in (Z) -2,6-dimethyllocta-5 , 7-diene-2,3-diol which is contained in said organic part.
- the nematicide composition further comprises at least one other active component other than the aqueous residue or hydrolate.
- the nematicidal composition consists exclusively of one of these three components mentioned: aqueous residue, its organic part or the active nematicidal component containing said organic part.
- the nematicidal composition comprises an amount of aqueous residue or hydrolate, or organic extract of said hydrolate sufficient to cause the mortality of 90% of an inoculum of infective juveniles, an amount equivalent to the effective dose of nematicidal action of the hydrolate, of its extract organic or of the active component nematicide that it contains.
- Said effective dose of hydrolate is 50%.
- the effective dose of the organic extract obtained from the hydrolate is 0.5 yg / ⁇ , therefore it is necessary to extract 0.5 ⁇ of hydrolate to obtain the effective dose of organic extract (0.5 yg).
- the natural nematicidal composition consists specifically of the aqueous residue or hydrolate, or in the organic component extracted from the hydrolate or in the active component extracted from said organic component or part of the residue. Any of these three components of the nematicidal composition is diluted by 50%.
- the fungicidal and nematicidal formulations against phytopathogens can be presented in the form of aqueous solution, powder, concentrated emulsion or microcapsules, among other forms of presentation and marketing known for this type of agricultural products.
- the use of the fungicidal formulation comprising the essential oil to control and / or eliminate phytopathogenic fungi in a crop can preferably be done by spraying said formulation on the plants of the crop. It should be understood herein that such use corresponds to a method for controlling and / or eliminating phytopathogenic fungi in a crop that comprises spraying the fungicidal formulation on the crop plants.
- the use of the nematicide formulation is composed only of the aqueous residue, of the organic extract obtained from the hydrolate or of the active component nematicide, including or not other additional components, to control phytopathogenic nematodes in a culture, can be preferably applied by applying said formulation, to the ground. It should also be understood from the present specification that said use corresponds to a method for controlling phytopathogenic nematodes in a culture comprising applying the nematicidal formulation on the soil.
- Figure 1 Simplified block diagram of a preferential practical embodiment of the phases of the process of extraction of derivatives of the Artemisia absinthium L. plant
- the invention is illustrated below by a preferred embodiment of the process for obtaining organic extracts according to the description given herein, as well as biological activity tests that have been carried out to determine the fungicidal and nematicidal activity of oils and their aqueous residues, respectively, of experimentally grown wormwood and obtained in three years of harvest (2008, 2009 and 2010).
- Example 1 Obtaining essential oil from the Artemisia absinthum L. plant with Candial variety.
- the extraction procedure basically comprises, as shown in Figure 1 attached, three distinct phases:
- a production methodology phase of said plant (1) a phase of extraction of organic extracts (2) in which said essential oil and a non-volatile extract (3) are obtained, in addition to the aqueous residues or hydrolates that are removed of the procedure, and
- the production methodology phase (1) includes the cultivation (6) in the field of the selected chemotype of the plant in question, by multiplication it is preferably carried out by means of cuttings or seeds in nursery-seedbed (7) for later planting in the seating area .
- This seating area is located in high areas with rainfall greater than 400-450 mm per year, and is worked by mechanized cultivation.
- the crop goes into production in the first year of its plantation, having to proceed to the collection (8) of the leaves and flowering tops when the plants are in the phenological stage of full flowering, then must proceed to drying (9) and later ground (10) of the biomass collected (11). Drying 89) is carried out in the shade, under air flow and for a period of approximately 8 days.
- the extraction phase of the organic extracts (2) is carried out by hydro-distillation and organic extraction (12) of the collected material (11), thus obtaining the oil essential and a non-volatile extract (3), in addition to an aqueous by-product or hydrolate, which is a process residue.
- Hydrodestilation is performed using a Clevenger type apparatus and organic extraction in a Sohxlet apparatus.
- An amount of 800 kg of biomass is introduced into the distillation vessel. in each distillation carried out, each distillation process with a duration of one hour and a half. From this process the essential oils are obtained, and also the hydrolate.
- the cooling rate of the device is between 150-200 liters, equivalent to the amount of hydrolates generated in each distillation. This amount varies depending on the ambient temperature.
- the extraction phase (4) of supercritical extracts (5) with CO 2 (22) of determined chemical composition is carried out using a compression pump (13) with a filter (14), an extraction cylinder (15), two collectors (16, 17), a cylindrical cooling device (18), a heat exchanger (19), a pressure sensor (20) and a flow meter (21).
- the collected material (11) is introduced into the extraction cylinder (15) and is symmetrically embedded with inert porous materials that allow a homogeneous flow of CO 2 (22), then heated until a temperature of 40 ° C, to then compress the pump (13) and CO 2 (22) until a pressure of 90 bar is achieved, at which time the supercritical fluid at the working pressure fills the extraction cylinder (15), adjusting in the two manifolds the pressure (16, 17), by means of the appropriate valves, and the temperature by means of the cooling device (18), such that the first of the manifolds (16) serves to eliminate heavy compounds, such as waxes, and the second collector (17) for the collection of the essential oil obtained as a supercritical extract (5).
- the average particle size value of the collected size used is 0.5 mm, and the gas flow through the extractor cylinder at 25 ° C and 1 atm. It is 10.5 1 / min.
- GC-MS mass gas chromatography
- Tables 2 and 3 are attached below with the annual yield of biomass and essential oil by population and year of A. absinthium. Table 2. Annual crop yield by population of A. absinthium (years 2008-2010) (Kg. Of biomass per hectare of
- Table 4 antifungal activity of wormwood oils, Candial variety 2008-2010 crops (for 2008-2009 the value of EC 5 p is included (ul / ml)
- NS Sierra Nevada Population (NC *): EC 5 o has not been calculated.
- Example 3 Nematicidal activity against nodule-forming nematodes: Meloidogyne javanica.
- the tests have been carried out according to the methodology described for Meloidogyne sp (Hernández-Carlos et al. 2011, Sosa et al. 2012) using in the trials the biological phase of juvenile infectives (J2) of Meloidogyne javanica.
- the activity of each product has been quantified at different concentrations, shown in Table 5, in at least four replicates.
- Each bioassay has been repeated at least three times and the nematosttatic / nematicidal activity has been determined from the percentage of immobilized infectious juveniles. dead.
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Mycology (AREA)
- Microbiology (AREA)
- Biotechnology (AREA)
- Pest Control & Pesticides (AREA)
- Botany (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Catching Or Destruction (AREA)
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP12871139.7A EP2826372A4 (en) | 2012-03-13 | 2012-03-13 | USE OF ESSENTIAL OILS, SUPERCRITICAL EXTRACTS AND AQUEOUS RESIDUES PRODUCED DURING A PROCESS FOR OBTAINING ORGANIC EXTRACTS FROM THE ARTEMISIA ABSINTHIUM PLANT |
AU2012373760A AU2012373760A1 (en) | 2012-03-13 | 2012-03-13 | Use of essential oils, supercritical extracts and aqueous residues generated during a process for obtaining organic extracts from the Artemisia absinthium L. plant |
PCT/ES2012/070162 WO2013135915A1 (es) | 2012-03-13 | 2012-03-13 | Uso de aceites esenciales, extractos supercríticos y residuos acuosos generados en un proceso de obtención de extractos orgánicos de la planta artemisia absinthium l |
US14/384,822 US20150030706A1 (en) | 2012-03-13 | 2012-03-13 | Use of essential oils, supercritical extracts and aqueous residues generated during a process for obtaining organic extracts from the artemisia absinthium l. plant |
MX2014010950A MX2014010950A (es) | 2012-03-13 | 2012-03-13 | Uso de aceites esenciales, extractos supercriticos y residuos acuosos generados en un proceso de obtencion de extractos organicos de la planta artemisia absinthium l. |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/ES2012/070162 WO2013135915A1 (es) | 2012-03-13 | 2012-03-13 | Uso de aceites esenciales, extractos supercríticos y residuos acuosos generados en un proceso de obtención de extractos orgánicos de la planta artemisia absinthium l |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2013135915A1 true WO2013135915A1 (es) | 2013-09-19 |
Family
ID=49160285
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/ES2012/070162 WO2013135915A1 (es) | 2012-03-13 | 2012-03-13 | Uso de aceites esenciales, extractos supercríticos y residuos acuosos generados en un proceso de obtención de extractos orgánicos de la planta artemisia absinthium l |
Country Status (5)
Country | Link |
---|---|
US (1) | US20150030706A1 (es) |
EP (1) | EP2826372A4 (es) |
AU (1) | AU2012373760A1 (es) |
MX (1) | MX2014010950A (es) |
WO (1) | WO2013135915A1 (es) |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN109111993B (zh) * | 2018-10-10 | 2022-01-14 | 湖北中烟工业有限责任公司 | 一种烟用酸枣显效组分的制备方法及其在卷烟中的应用 |
CN109452319B (zh) * | 2018-12-19 | 2021-04-23 | 江西省农业科学院植物保护研究所 | 一种高效防治芦笋茎枯病的组合物及其应用 |
CN112868676B (zh) * | 2021-02-08 | 2022-03-01 | 上海交通大学 | 一种用于防治十字花科植物根肿病的植物源组合提取液 |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2076896B1 (es) | 1993-12-08 | 1996-08-16 | Tae Woo Yoo | Procedimiento para producir moxas. |
WO2002049600A1 (en) | 2000-12-20 | 2002-06-27 | Quest International B.V. | Perfume compositions |
US20080107640A1 (en) * | 1997-01-09 | 2008-05-08 | Tvedten Stephen L | Biological pesticide |
WO2012013590A2 (en) * | 2010-07-26 | 2012-02-02 | Bayer Cropscience Ag | Use of succinate dehydrogenase inhibitors and/or respiratory chain complex iii inhibitors for improving the ratio of harmful to beneficial microorganisms |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4960754A (en) * | 1987-01-09 | 1990-10-02 | International Flavors & Fragrances Inc. | 3,7-dimethyl-6,7-dioxo-1,3-octadiene derivatives and organoleptic uses thereof |
-
2012
- 2012-03-13 US US14/384,822 patent/US20150030706A1/en not_active Abandoned
- 2012-03-13 WO PCT/ES2012/070162 patent/WO2013135915A1/es active Application Filing
- 2012-03-13 EP EP12871139.7A patent/EP2826372A4/en not_active Withdrawn
- 2012-03-13 MX MX2014010950A patent/MX2014010950A/es unknown
- 2012-03-13 AU AU2012373760A patent/AU2012373760A1/en not_active Abandoned
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2076896B1 (es) | 1993-12-08 | 1996-08-16 | Tae Woo Yoo | Procedimiento para producir moxas. |
US20080107640A1 (en) * | 1997-01-09 | 2008-05-08 | Tvedten Stephen L | Biological pesticide |
WO2002049600A1 (en) | 2000-12-20 | 2002-06-27 | Quest International B.V. | Perfume compositions |
WO2012013590A2 (en) * | 2010-07-26 | 2012-02-02 | Bayer Cropscience Ag | Use of succinate dehydrogenase inhibitors and/or respiratory chain complex iii inhibitors for improving the ratio of harmful to beneficial microorganisms |
Non-Patent Citations (7)
Title |
---|
"Comparative chemistry and insect antifeedant action of traditional (Clevenger and Soxhlet) and supercritical extracts (C0 ) of two cultivated wormwood (Artemisia absinthium L.) populations", IND. CROP. PROD., vol. 34, 2011, pages 1615 - 1621 |
GHASEMI E. ET AL.: "Comparitive analysis of the oil and supercritical C02 extract of Artemisia sieberi", JOURNAL OF FOOD ENGINEERING, vol. 79, 10 March 2006 (2006-03-10), pages 306 - 311, XP005664712 * |
GONZALEZ-COLOMA A. ET AL.: "Major components of Spanish cultivated Artemisia absinthium populations: antifeedant, antiparasitic, and antioxidant effects", INDUSTRIAL CROPS AND PRODUCTS, vol. 37, 25 January 2012 (2012-01-25), pages 401 - 407, XP055153781 * |
L. MARTIN ET AL.: "Supercritical fluid extraction of wormwood (Artemisia absinthium L.)", J. SUPERCRIT. FLUIDS, vol. 56, 2011, pages 64 - 71, XP055153780, DOI: doi:10.1016/j.supflu.2010.11.017 |
MARTIN L. ET AL.: "Comparative chemistry and insect antifeedant action of traditional(Clevenger and Soxhlet) and supercritical extracts (C02) of two cultivated wormwood (Artemisia absinthium L.) populations", INDUSTRIAL CROPS AND PRODUCTS, vol. 34, 24 June 2011 (2011-06-24), pages 1615 - 1621, XP055017296 * |
MARTIN L. ET AL.: "Supercritical fluid extraction of wormwood (Artemisia absinthium L.)", THE JOURNAL OF SUPERCRITICAL FLUIDS, vol. 56, 2011, pages 64 - 70, XP055153780 * |
See also references of EP2826372A4 |
Also Published As
Publication number | Publication date |
---|---|
EP2826372A1 (en) | 2015-01-21 |
US20150030706A1 (en) | 2015-01-29 |
AU2012373760A1 (en) | 2014-10-16 |
MX2014010950A (es) | 2015-02-24 |
EP2826372A4 (en) | 2015-08-26 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
Pavela et al. | New knowledge for yield, composition and insecticidal activity of essential oils obtained from the aerial parts or seeds of fennel (Foeniculum vulgare Mill.) | |
Boursier et al. | Are traditional neem extract preparations as efficient as a commercial formulation of azadirachtin A? | |
Andrés et al. | Nematicidal potential of hydrolates from the semi industrial vapor-pressure extraction of Spanish aromatic plants | |
CN101223892A (zh) | 含有川楝素的组合物杀虫剂及其制备方法 | |
CN103931678B (zh) | 一种防治迟眼蕈蚊的生物农药及其制备工艺 | |
WO2021148684A1 (es) | Composiciones biopesticidas que comprenden extractos vegetales y su uso fitosanitario | |
CN104872218B (zh) | 一种含山茶皂苷的天然家庭杀虫剂 | |
CN100411522C (zh) | 生物农药组合物及其制备方法和用途 | |
CN104073362A (zh) | 青蒿挥发油的提取方法、其产品及应用 | |
WO2013135915A1 (es) | Uso de aceites esenciales, extractos supercríticos y residuos acuosos generados en un proceso de obtención de extractos orgánicos de la planta artemisia absinthium l | |
Ahuja et al. | An ethnomedical, phytochemical and pharmacological profile of Artemisia parviflora Roxb | |
CN104886168A (zh) | 一种防治番茄青枯病的生物农药及制备方法 | |
Mouna et al. | Insecticidal effect of two aqueous extracts from the leaves of Salvia officinalis and Eucalyptus camaldulensis against Aphis fabae | |
Arutselvi et al. | Formulation of natural insecticides against Panchaetothrips indicus Bagnall in Curcuma longa L. leaves of PTS and Erode varieties | |
ES2405210B1 (es) | Procedimiento de extracción de derivados bioinsecticidas de la planta artemisia absinthium l. | |
KR20130080667A (ko) | 후추 속 식물과 라반듈라 속 식물 추출물을 함유하는 살충용 조성물 | |
CN112471179A (zh) | 砂蓝刺头在杀虫杀螨方面的用途及其生物防治药剂和制备方法 | |
CN101129142A (zh) | 一种植物杀虫剂及其制备方法和应用 | |
CN104286012A (zh) | 一种含有氟啶虫胺腈、氯氰菊酯、辛硫磷和螺虫乙酯的高效杀虫剂 | |
ES2743403T3 (es) | Repelentes de plagas de extractos de plantas | |
Mukhtar et al. | Meticulous approach towards pharmacognosy and socio-economic impact of ethnomedicinal plant: Ocimum kilimandscharicum | |
KR102060196B1 (ko) | 머귀나무 종자 추출물을 포함하는 살충제 조성물 및 이를 이용한 살충방법 | |
Abate et al. | Artemisia annua l. As an alternative potential weed control option | |
WO2020067867A1 (es) | Plaguicida agrícola con extractos de allium sativum y heliopsis longipes | |
CN105638691B (zh) | 环小萼苔醇-3-咖啡酸酯在制备杀虫剂中应用 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application |
Ref document number: 12871139 Country of ref document: EP Kind code of ref document: A1 |
|
WWE | Wipo information: entry into national phase |
Ref document number: 14201040 Country of ref document: CO Ref document number: MX/A/2014/010950 Country of ref document: MX |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
WWE | Wipo information: entry into national phase |
Ref document number: 14384822 Country of ref document: US |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2012871139 Country of ref document: EP |
|
ENP | Entry into the national phase |
Ref document number: 2012373760 Country of ref document: AU Date of ref document: 20120313 Kind code of ref document: A |