CA2808489C - Anti-microbial compositions - Google Patents
Anti-microbial compositions Download PDFInfo
- Publication number
- CA2808489C CA2808489C CA2808489A CA2808489A CA2808489C CA 2808489 C CA2808489 C CA 2808489C CA 2808489 A CA2808489 A CA 2808489A CA 2808489 A CA2808489 A CA 2808489A CA 2808489 C CA2808489 C CA 2808489C
- Authority
- CA
- Canada
- Prior art keywords
- galactofuranose
- plant
- beta
- galactopyranose
- epipyrone
- 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.)
- Active
Links
- 230000000845 anti-microbial effect Effects 0.000 title claims abstract description 10
- 239000000203 mixture Substances 0.000 title claims description 28
- 239000004599 antimicrobial Substances 0.000 title claims description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 37
- 238000000034 method Methods 0.000 claims description 35
- 206010017533 Fungal infection Diseases 0.000 claims description 15
- 208000031888 Mycoses Diseases 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 239000012453 solvate Substances 0.000 claims description 15
- 235000013399 edible fruits Nutrition 0.000 claims description 5
- 235000013311 vegetables Nutrition 0.000 claims description 5
- 244000038559 crop plants Species 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 4
- 241001465180 Botrytis Species 0.000 claims description 3
- 241001121967 Lecanicillium Species 0.000 claims description 3
- 239000003814 drug Substances 0.000 claims description 3
- 230000002401 inhibitory effect Effects 0.000 claims description 3
- 230000002265 prevention Effects 0.000 claims description 3
- 241000702141 Corynephage beta Species 0.000 claims 20
- 241000687983 Cerobasis alpha Species 0.000 claims 10
- WQZGKKKJIJFFOK-FPRJBGLDSA-N beta-D-galactose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-FPRJBGLDSA-N 0.000 claims 1
- 241001506775 Epicoccum nigrum Species 0.000 abstract description 15
- 208000015181 infectious disease Diseases 0.000 abstract description 6
- 230000000813 microbial effect Effects 0.000 abstract description 6
- 241001465754 Metazoa Species 0.000 abstract description 5
- 241000233866 Fungi Species 0.000 abstract description 4
- 241000123650 Botrytis cinerea Species 0.000 abstract description 3
- 241001121966 Lecanicillium muscarium Species 0.000 abstract description 3
- 230000000855 fungicidal effect Effects 0.000 abstract description 3
- 239000002207 metabolite Substances 0.000 abstract description 2
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 2
- 244000052769 pathogen Species 0.000 abstract 1
- 244000000003 plant pathogen Species 0.000 abstract 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 238000004128 high performance liquid chromatography Methods 0.000 description 26
- 241000196324 Embryophyta Species 0.000 description 23
- 239000000284 extract Substances 0.000 description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 239000000126 substance Substances 0.000 description 15
- 150000002500 ions Chemical class 0.000 description 13
- 239000000523 sample Substances 0.000 description 13
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 10
- 238000002474 experimental method Methods 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 239000000469 ethanolic extract Substances 0.000 description 8
- 238000000605 extraction Methods 0.000 description 8
- GDSQFNQIWJCATH-PHOXTJPWSA-N (2z,3e,5e,7e,9e,11e,13e)-14-[(2r,3r,4s)-3,4-dihydroxy-5-oxo-2-(1,2,3-trihydroxypropyl)-3,4-dihydro-2h-pyrano[3,2-c]pyran-7-yl]-2-(2,4-dimethylhexylidene)-4-methyltetradeca-3,5,7,9,11,13-hexaenoic acid Chemical compound O1[C@@H](C(O)C(O)CO)[C@H](O)[C@@H](O)C2=C1C=C(/C=C/C=C/C=C/C=C/C=C/C(/C)=C/C(=C/C(C)CC(C)CC)/C(O)=O)OC2=O GDSQFNQIWJCATH-PHOXTJPWSA-N 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 238000001360 collision-induced dissociation Methods 0.000 description 6
- 239000000417 fungicide Substances 0.000 description 6
- 239000000049 pigment Substances 0.000 description 6
- 150000003214 pyranose derivatives Chemical class 0.000 description 6
- 238000002211 ultraviolet spectrum Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 238000013467 fragmentation Methods 0.000 description 5
- 238000006062 fragmentation reaction Methods 0.000 description 5
- 230000037361 pathway Effects 0.000 description 5
- 238000002390 rotary evaporation Methods 0.000 description 5
- 238000001896 rotating frame Overhauser effect spectroscopy Methods 0.000 description 5
- 244000000626 Daucus carota Species 0.000 description 4
- 235000002767 Daucus carota Nutrition 0.000 description 4
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 238000010790 dilution Methods 0.000 description 4
- 239000012895 dilution Substances 0.000 description 4
- 230000002538 fungal effect Effects 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 239000006228 supernatant Substances 0.000 description 4
- 239000001052 yellow pigment Substances 0.000 description 4
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical group O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 230000021736 acetylation Effects 0.000 description 3
- 238000006640 acetylation reaction Methods 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- 235000011114 ammonium hydroxide Nutrition 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000004949 mass spectrometry Methods 0.000 description 3
- 235000011007 phosphoric acid Nutrition 0.000 description 3
- RYVMUASDIZQXAA-UHFFFAOYSA-N pyranoside Natural products O1C2(OCC(C)C(OC3C(C(O)C(O)C(CO)O3)O)C2)C(C)C(C2(CCC3C4(C)CC5O)C)C1CC2C3CC=C4CC5OC(C(C1O)O)OC(CO)C1OC(C1OC2C(C(OC3C(C(O)C(O)C(CO)O3)O)C(O)C(CO)O2)O)OC(CO)C(O)C1OC1OCC(O)C(O)C1O RYVMUASDIZQXAA-UHFFFAOYSA-N 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- WKKJIKPTKYQIHK-UHFFFAOYSA-N tetradeca-3,5,7,9,11,13-hexaenoic acid Chemical compound OC(=O)CC=CC=CC=CC=CC=CC=C WKKJIKPTKYQIHK-UHFFFAOYSA-N 0.000 description 3
- 238000001551 total correlation spectroscopy Methods 0.000 description 3
- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- OENHQHLEOONYIE-UKMVMLAPSA-N all-trans beta-carotene Natural products CC=1CCCC(C)(C)C=1/C=C/C(/C)=C/C=C/C(/C)=C/C=C/C=C(C)C=CC=C(C)C=CC1=C(C)CCCC1(C)C OENHQHLEOONYIE-UKMVMLAPSA-N 0.000 description 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 2
- 239000011648 beta-carotene Substances 0.000 description 2
- 235000013734 beta-carotene Nutrition 0.000 description 2
- TUPZEYHYWIEDIH-WAIFQNFQSA-N beta-carotene Natural products CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C)C=CC=C(/C)C=CC2=CCCCC2(C)C TUPZEYHYWIEDIH-WAIFQNFQSA-N 0.000 description 2
- 229960002747 betacarotene Drugs 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000001793 charged compounds Chemical class 0.000 description 2
- 230000001143 conditioned effect Effects 0.000 description 2
- 238000005100 correlation spectroscopy Methods 0.000 description 2
- 230000008878 coupling Effects 0.000 description 2
- 238000010168 coupling process Methods 0.000 description 2
- 238000005859 coupling reaction Methods 0.000 description 2
- 238000002518 distortionless enhancement with polarization transfer Methods 0.000 description 2
- COJARPHAKVBMFD-UHFFFAOYSA-N flavipin Chemical compound CC1=C(O)C(O)=C(O)C(C=O)=C1C=O COJARPHAKVBMFD-UHFFFAOYSA-N 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 229960003082 galactose Drugs 0.000 description 2
- 230000035784 germination Effects 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- 238000009630 liquid culture Methods 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 238000005016 nuclear Overhauser enhanced spectroscopy Methods 0.000 description 2
- 239000001053 orange pigment Substances 0.000 description 2
- 239000008363 phosphate buffer Substances 0.000 description 2
- 239000001965 potato dextrose agar Substances 0.000 description 2
- 229940002612 prodrug Drugs 0.000 description 2
- 239000000651 prodrug Substances 0.000 description 2
- 239000013557 residual solvent Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- OENHQHLEOONYIE-JLTXGRSLSA-N β-Carotene Chemical compound CC=1CCCC(C)(C)C=1\C=C\C(\C)=C\C=C\C(\C)=C\C=C\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C OENHQHLEOONYIE-JLTXGRSLSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 229930182476 C-glycoside Natural products 0.000 description 1
- 150000000700 C-glycosides Chemical class 0.000 description 1
- 241000321538 Candidia Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 241000713772 Human immunodeficiency virus 1 Species 0.000 description 1
- 230000004570 RNA-binding Effects 0.000 description 1
- 108020000999 Viral RNA Proteins 0.000 description 1
- 238000002835 absorbance Methods 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 230000001093 anti-cancer Effects 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 150000007514 bases Chemical class 0.000 description 1
- 230000027455 binding Effects 0.000 description 1
- 238000006065 biodegradation reaction Methods 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 229910021538 borax Inorganic materials 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- TZLFGPZAGYEXAS-IMQJRXMUSA-N epicoccamide Natural products C[C@@H](CCCCCCCCCCCCCCO[C@@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O)C(=O)C2=C(C)N(C)[C@@H](C)C2=O TZLFGPZAGYEXAS-IMQJRXMUSA-N 0.000 description 1
- 229940049152 epicoccum nigrum extract Drugs 0.000 description 1
- 238000002481 ethanol extraction Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 210000000416 exudates and transudate Anatomy 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 102000034356 gene-regulatory proteins Human genes 0.000 description 1
- 108091006104 gene-regulatory proteins Proteins 0.000 description 1
- 238000001052 heteronuclear multiple bond coherence spectrum Methods 0.000 description 1
- 231100000086 high toxicity Toxicity 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000002952 polymeric resin Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000012521 purified sample Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000004763 spore germination Effects 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 238000004885 tandem mass spectrometry Methods 0.000 description 1
- BSVBQGMMJUBVOD-UHFFFAOYSA-N trisodium borate Chemical compound [Na+].[Na+].[Na+].[O-]B([O-])[O-] BSVBQGMMJUBVOD-UHFFFAOYSA-N 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/365—Lactones
- A61K31/366—Lactones having six-membered rings, e.g. delta-lactones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
-
- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
-
- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
- A01N43/16—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with oxygen as the ring hetero atom
-
- 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
- A01N49/00—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds containing the group, wherein m+n>=1, both X together may also mean —Y— or a direct carbon-to-carbon bond, and the carbon atoms marked with an asterisk are not part of any ring system other than that which may be formed by the atoms X, the carbon atoms in square brackets being part of any acyclic or cyclic structure, or the group, wherein A means a carbon atom or Y, n>=0, and not more than one of these carbon atoms being a member of the same ring system, e.g. juvenile insect hormones or mimics thereof
-
- 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
- A01N63/00—Biocides, pest repellants or attractants, or plant growth regulators containing microorganisms, viruses, microbial fungi, animals or substances produced by, or obtained from, microorganisms, viruses, microbial fungi or animals, e.g. enzymes or fermentates
- A01N63/30—Microbial fungi; Substances produced thereby or obtained therefrom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Wood Science & Technology (AREA)
- Agronomy & Crop Science (AREA)
- Environmental Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Molecular Biology (AREA)
- Epidemiology (AREA)
- Biotechnology (AREA)
- Microbiology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Insects & Arthropods (AREA)
- Mycology (AREA)
- Virology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicines Containing Plant Substances (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NZ587490 | 2010-08-20 | ||
| NZ587490A NZ587490A (en) | 2010-08-20 | 2010-08-20 | Anti-Microbial Compounds containing compounds with a sugar substituent |
| PCT/NZ2011/000164 WO2012023865A1 (en) | 2010-08-20 | 2011-08-22 | Anti-microbial compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2808489A1 CA2808489A1 (en) | 2012-02-23 |
| CA2808489C true CA2808489C (en) | 2018-10-16 |
Family
ID=45605341
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2808489A Active CA2808489C (en) | 2010-08-20 | 2011-08-22 | Anti-microbial compositions |
Country Status (10)
| Country | Link |
|---|---|
| US (3) | US8889636B2 (OSRAM) |
| EP (1) | EP2605654B1 (OSRAM) |
| JP (1) | JP5956439B2 (OSRAM) |
| KR (1) | KR101903200B1 (OSRAM) |
| CN (2) | CN103167802B (OSRAM) |
| AU (1) | AU2011292510B2 (OSRAM) |
| CA (1) | CA2808489C (OSRAM) |
| ES (1) | ES2966573T3 (OSRAM) |
| NZ (1) | NZ587490A (OSRAM) |
| WO (1) | WO2012023865A1 (OSRAM) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ587490A (en) * | 2010-08-20 | 2013-03-28 | Greentide Ltd | Anti-Microbial Compounds containing compounds with a sugar substituent |
| CN107779403B (zh) * | 2016-08-29 | 2019-11-12 | 江苏省农业科学院 | 一种生防真菌黑附球菌h5及其应用 |
| EP3360549A1 (en) | 2017-02-14 | 2018-08-15 | Rheinische Friedrich-Wilhelms-Universität Bonn | Small molecule therapeutics for treating metachromatic leukodystrophy |
| CN108165589B (zh) * | 2017-12-23 | 2021-02-05 | 安徽工程大学 | 一种真菌花色苷类红素及其发酵制备方法 |
| CN112358974B (zh) * | 2020-12-09 | 2022-06-10 | 昆明理工大学 | 一株植物内生真菌黑附球菌fzt214及其应用 |
| US11751684B2 (en) | 2021-07-22 | 2023-09-12 | Jean Francois Bedard | Rod holder |
Family Cites Families (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002047281A (ja) * | 2000-07-28 | 2002-02-12 | Mitsubishi-Tokyo Pharmaceuticals Inc | テロメレース阻害剤 |
| CA2758968C (en) * | 2009-04-22 | 2018-05-29 | Axikin Pharmaceuticals, Inc. | 2,5-disubstituted arylsulfonamide ccr3 antagonists |
| JO3416B1 (ar) * | 2009-04-27 | 2019-10-20 | Jeneil Biosurfactant Co Llc | تركيبات مضادة للبكتيريا وطرق استخدامها |
| US20110136729A1 (en) * | 2009-05-26 | 2011-06-09 | Shien Lu | Occidiofungin, a unique antifungal glycopeptide produced by a strain of burkholderia contaminans |
| EP2269454A1 (en) * | 2009-06-24 | 2011-01-05 | Bayer CropScience AG | Combinations of fungicidally active yeast and fungicides |
| CA2772937C (en) * | 2009-09-03 | 2018-07-17 | Fbsciences Holdings, Inc. | Seed treatment compositions & methods |
| GB2473460B (en) * | 2009-09-10 | 2016-02-10 | Univ Surrey | Antimicrobial Composition |
| GB2474251A (en) * | 2009-10-08 | 2011-04-13 | Uws Ventures Ltd | Antimicrobial composition and method of controlling contamination or infections using said composition |
| NL1037411C2 (nl) * | 2009-10-23 | 2011-04-27 | Pk Peters Krizman Sa | Samenstelling omvattende anijszuur, een derivaat daarvan en/of een farmaceutisch acceptabel zout hiervan en een zure buffer, evenals een doseringsvorm en toepassingen hiervan. |
| GB2475359A (en) * | 2009-11-11 | 2011-05-18 | Biocopea Ltd | A compound for use in treating a fulminant respiratory disorder |
| AT509501B1 (de) * | 2010-02-24 | 2012-06-15 | Univ Wien Tech | Pflanzenschutzmittel |
| AR080234A1 (es) * | 2010-02-25 | 2012-03-21 | Marrone Bio Innovations Inc | Cepa bacteriana aislada del genero burkholderia y metabolitos pesticidas del mismo |
| US9288996B2 (en) * | 2010-03-18 | 2016-03-22 | Basf Se | Fungicidal compositions comprising a phosphate solubilizing microorganism and a fungicidally active compound |
| SI23311A (sl) * | 2010-03-19 | 2011-09-30 | Kemijski inštitut | Farmacevtska kombinacija acetilsalicilne kisline in protiglivne substance za uničevanje ali inhibicijo rasti in replikacije gliv |
| UA107963C2 (xx) * | 2010-06-07 | 2015-03-10 | Janssen Pharmaceutica Nv | ПРОТИГРИБКОВІ ПОХІДНІ 5,6-ДИГІДРО-4-$(ДИФТОРЕТИЛ)ФЕНІЛ]-4H-ПІРОЛО$1,2-a]$1,4]БЕНЗОДІАЗЕПІНУ І 4-(ДИФТОРЕТИЛ)ФЕНІЛ-6H-ПІРОЛО$1,2-a]$1,4]БЕНЗОДІАЗЕПІНУ |
| KR101869524B1 (ko) * | 2010-07-26 | 2018-07-20 | 바이엘 인텔렉쳐 프로퍼티 게엠베하 | 유해 미생물 대 유용 미생물의 비율을 개선하기 위한 숙시네이트 데히드로게나제 저해제 및/또는 호흡사슬컴플렉스 iii 저해제의 용도 |
| NZ587490A (en) * | 2010-08-20 | 2013-03-28 | Greentide Ltd | Anti-Microbial Compounds containing compounds with a sugar substituent |
| BR112013006660A2 (pt) * | 2010-09-23 | 2016-06-07 | Globachem | uso de uma composição para o aumento de rendimento de cultura |
| AR083112A1 (es) * | 2010-10-01 | 2013-01-30 | Syngenta Participations Ag | Metodo para controlar enfermedades fitopatogenas y composiciones fungicidas utiles para dicho control |
| PT105331A (pt) * | 2010-10-12 | 2012-04-12 | Cev Biotecnologia Das Plantas S A | Conservante alimentar |
| TW201225844A (en) * | 2010-10-25 | 2012-07-01 | Marrone Bio Innovations Inc | Chromobacterium bioactive compositions and metabolites |
| RU2448960C1 (ru) * | 2010-12-06 | 2012-04-27 | Виктор Вениаминович Тец | Фунгицидное средство |
| RO126736B1 (ro) * | 2010-12-08 | 2012-11-29 | Institutul Naţional De Cercetare-Dezvoltare Pentru Pedologie, Agrochimie Şi Protecţia Mediului | Tulpini de botrytis cinerea producătoare de elicitori fungici, produs pentru imunizarea plantelor de căpşun contra agenţilor putregaiului cenuşiu şi metodă de aplicare |
| EP3216798A3 (en) * | 2010-12-09 | 2017-10-25 | Wockhardt Limited | Ketolide compounds |
| EP2663582B1 (en) * | 2011-01-13 | 2018-07-11 | Austin Research Labs Corp. | High load dispersions for treating infections |
| EP3295797A1 (en) * | 2011-03-23 | 2018-03-21 | Bayer Intellectual Property GmbH | Active compound combinations |
| EP2532232A1 (en) * | 2011-06-10 | 2012-12-12 | InterMed Discovery GmbH | Long chain glycolipids useful to avoid perishing or microbial contamination of materials |
-
2010
- 2010-08-20 NZ NZ587490A patent/NZ587490A/xx unknown
-
2011
- 2011-08-22 WO PCT/NZ2011/000164 patent/WO2012023865A1/en not_active Ceased
- 2011-08-22 EP EP11818451.4A patent/EP2605654B1/en active Active
- 2011-08-22 CN CN201180050429.6A patent/CN103167802B/zh active Active
- 2011-08-22 KR KR1020137007020A patent/KR101903200B1/ko active Active
- 2011-08-22 JP JP2013525861A patent/JP5956439B2/ja active Active
- 2011-08-22 ES ES11818451T patent/ES2966573T3/es active Active
- 2011-08-22 AU AU2011292510A patent/AU2011292510B2/en active Active
- 2011-08-22 CN CN201610064680.2A patent/CN105640941A/zh active Pending
- 2011-08-22 CA CA2808489A patent/CA2808489C/en active Active
- 2011-08-24 US US13/216,443 patent/US8889636B2/en active Active
-
2014
- 2014-08-21 US US14/464,747 patent/US20140357580A1/en not_active Abandoned
-
2015
- 2015-10-05 US US14/874,633 patent/US20160021881A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CN103167802B (zh) | 2016-04-13 |
| EP2605654A4 (en) | 2014-01-22 |
| EP2605654A1 (en) | 2013-06-26 |
| US20140357580A1 (en) | 2014-12-04 |
| EP2605654C0 (en) | 2023-09-27 |
| AU2011292510A1 (en) | 2013-03-28 |
| JP2013539466A (ja) | 2013-10-24 |
| CN103167802A (zh) | 2013-06-19 |
| KR101903200B1 (ko) | 2018-10-01 |
| WO2012023865A1 (en) | 2012-02-23 |
| KR20140023864A (ko) | 2014-02-27 |
| EP2605654B1 (en) | 2023-09-27 |
| JP5956439B2 (ja) | 2016-07-27 |
| US20120108526A1 (en) | 2012-05-03 |
| NZ587490A (en) | 2013-03-28 |
| US20160021881A1 (en) | 2016-01-28 |
| CA2808489A1 (en) | 2012-02-23 |
| AU2011292510B2 (en) | 2015-08-20 |
| CN105640941A (zh) | 2016-06-08 |
| ES2966573T3 (es) | 2024-04-23 |
| US8889636B2 (en) | 2014-11-18 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Stuardo et al. | Antifungal properties of quinoa (Chenopodium quinoa Willd) alkali treated saponins against Botrytis cinerea | |
| US20160021881A1 (en) | Anti-microbial compositions | |
| Majouli et al. | Phytochemical analysis and biological activities of Hertia cheirifolia L. roots extracts | |
| KR101877932B1 (ko) | 그람미신 화합물을 유효성분으로 함유하는 선충 방제용 조성물 및 이의 용도 | |
| Christensen | Tuliposides from Tulipa sylvestris and T. turkestanica | |
| Yusnawan | The effectiveness of polar and non polar fractions of Ageratum conyzoides l. to control peanut rust disease and phytochemical screenings of secondary metabolites | |
| Saravana Kumar et al. | Rapid isolation of ricinine, a pyridone alkaloid from Ricinus communis (L.) with antifungal properties | |
| Castañeda-Gómez et al. | Acylsugar diversity in the resin glycosides from Ipomoea tricolor seeds as chemosensitizers in breast cancer cells | |
| Maienfisch | Challenges and risks associated with impurity profiles in technical grade crop protection products produced semi-synthetically from natural products | |
| Ivarsen et al. | Bioassay-guided chromatographic isolation and identification of antibacterial compounds from Artemisia annua L. that inhibit Clostridium perfringens growth | |
| Kulesh et al. | Antioxidant activity of the isoflavonoids from the roots of Maackia amurensis | |
| US20150126465A1 (en) | Process for producing derivatives of pyrostegia venusta, derivatives of pyrostegia venusta, pharmaceutical compositions and its uses | |
| Muth et al. | Differential metabolic response of narrow leafed lupine (Lupinus angustifolius) leaves to infection with Colletotrichum lupini | |
| Pacciaroni et al. | Antifungal activity of Heterothalamus alienus metabolites | |
| Zhao et al. | New and antifungal diterpenoids of sunflower against gray mold | |
| Passera et al. | Evaluation of the biocide activity of tomatine-rich extracts from tomato cannery residues against fungi and bacteria | |
| CN109090115B (zh) | 一种山奈酚(4-o-甲基)葡萄糖苷类化合物在抗虫药剂中的应用 | |
| US20070154574A1 (en) | Fungicides compositions comprising the extract of Chloranthus henryi and a novel sesquiterpene compound isolated from them | |
| KR100713857B1 (ko) | 여로 추출물과 이로부터 분리된 베라트라민을 유효성분으로하는 농업용 살균제 조성물 | |
| KR100543977B1 (ko) | 키틴합성효소 ⅱ의 저해 활성을 지니는 홀아비꽃대추출물과 이로부터 분리된 신규 활성 화합물 | |
| WO2018116054A1 (en) | Compounds with fungicidal activity | |
| CN106912489A (zh) | 阿维菌素类衍生物的制备方法及其应用 | |
| Patole et al. | HPTLC profile of solvent extracts of neem and gorakhmundi | |
| KR20070107853A (ko) | 리그난계 화합물, 레조시놀계 화합물 또는 이를 포함하는육두구 추출물을 함유하는 식물병 방제용 조성물 및 이를이용한 식물병 방제방법 | |
| CN110551097A (zh) | 单炔类化合物及其制备方法和用途 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20160822 |