OA13354A - Synthetic compounds useful as nodulation agents ofleguminous plants and preparation processes thereof. - Google Patents
Synthetic compounds useful as nodulation agents ofleguminous plants and preparation processes thereof. Download PDFInfo
- Publication number
- OA13354A OA13354A OA1200600218A OA1200600218A OA13354A OA 13354 A OA13354 A OA 13354A OA 1200600218 A OA1200600218 A OA 1200600218A OA 1200600218 A OA1200600218 A OA 1200600218A OA 13354 A OA13354 A OA 13354A
- Authority
- OA
- OAPI
- Prior art keywords
- alkyl
- represent
- fucosyl
- chosen
- substituent chosen
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 120
- 230000024121 nodulation Effects 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title 1
- 235000021374 legumes Nutrition 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 15
- 125000001424 substituent group Chemical group 0.000 claims description 165
- 229910052739 hydrogen Inorganic materials 0.000 claims description 126
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 114
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 112
- -1 acetylfucosyl Chemical group 0.000 claims description 104
- 125000002446 fucosyl group Chemical group C1([C@@H](O)[C@H](O)[C@H](O)[C@@H](O1)C)* 0.000 claims description 88
- 229910006069 SO3H Inorganic materials 0.000 claims description 77
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 77
- 229910006145 SO3Li Inorganic materials 0.000 claims description 76
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 57
- 229910052757 nitrogen Inorganic materials 0.000 claims description 57
- 125000005842 heteroatom Chemical group 0.000 claims description 56
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 55
- 239000011593 sulfur Substances 0.000 claims description 55
- 229910052717 sulfur Inorganic materials 0.000 claims description 55
- 229920006395 saturated elastomer Polymers 0.000 claims description 52
- 125000004432 carbon atom Chemical group C* 0.000 claims description 49
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 43
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 43
- 239000001301 oxygen Substances 0.000 claims description 40
- 229910052760 oxygen Inorganic materials 0.000 claims description 40
- 241000196324 Embryophyta Species 0.000 claims description 37
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 36
- 239000011734 sodium Substances 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 30
- 125000003118 aryl group Chemical group 0.000 claims description 29
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 28
- 125000000089 arabinosyl group Chemical group C1([C@@H](O)[C@H](O)[C@H](O)CO1)* 0.000 claims description 25
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 22
- 229910052736 halogen Inorganic materials 0.000 claims description 21
- 150000002367 halogens Chemical class 0.000 claims description 21
- 229910052799 carbon Inorganic materials 0.000 claims description 20
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 19
- 229910052708 sodium Inorganic materials 0.000 claims description 19
- 239000004215 Carbon black (E152) Substances 0.000 claims description 18
- 125000004429 atom Chemical group 0.000 claims description 18
- 229930195733 hydrocarbon Natural products 0.000 claims description 18
- 150000002430 hydrocarbons Chemical class 0.000 claims description 18
- 125000000732 arylene group Chemical group 0.000 claims description 16
- 125000005549 heteroarylene group Chemical group 0.000 claims description 16
- 125000004957 naphthylene group Chemical group 0.000 claims description 14
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 12
- 101100240526 Caenorhabditis elegans nhr-20 gene Proteins 0.000 claims description 12
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 claims description 12
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 12
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 claims description 12
- 150000001204 N-oxides Chemical class 0.000 claims description 12
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 12
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims description 12
- 229910052744 lithium Inorganic materials 0.000 claims description 12
- 229910052752 metalloid Inorganic materials 0.000 claims description 12
- 150000002738 metalloids Chemical class 0.000 claims description 12
- 229910052700 potassium Inorganic materials 0.000 claims description 12
- 239000011591 potassium Substances 0.000 claims description 12
- 150000003457 sulfones Chemical class 0.000 claims description 12
- 150000003462 sulfoxides Chemical class 0.000 claims description 11
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims description 10
- 230000003287 optical effect Effects 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 244000068988 Glycine max Species 0.000 claims description 7
- 235000010469 Glycine max Nutrition 0.000 claims description 7
- 230000008569 process Effects 0.000 claims description 5
- 240000004713 Pisum sativum Species 0.000 claims description 4
- 235000010582 Pisum sativum Nutrition 0.000 claims description 4
- 240000006677 Vicia faba Species 0.000 claims description 4
- 150000005621 tetraalkylammonium salts Chemical class 0.000 claims description 4
- 244000105624 Arachis hypogaea Species 0.000 claims description 3
- 235000010777 Arachis hypogaea Nutrition 0.000 claims description 3
- 244000046052 Phaseolus vulgaris Species 0.000 claims description 3
- 235000010627 Phaseolus vulgaris Nutrition 0.000 claims description 3
- 235000003276 Apios tuberosa Nutrition 0.000 claims description 2
- 235000010744 Arachis villosulicarpa Nutrition 0.000 claims description 2
- 102100028717 Cytosolic 5'-nucleotidase 3A Human genes 0.000 claims description 2
- 241000219745 Lupinus Species 0.000 claims description 2
- 235000002096 Vicia faba var. equina Nutrition 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 21
- SGPGESCZOCHFCL-UHFFFAOYSA-N Tilisolol hydrochloride Chemical compound [Cl-].C1=CC=C2C(=O)N(C)C=C(OCC(O)C[NH2+]C(C)(C)C)C2=C1 SGPGESCZOCHFCL-UHFFFAOYSA-N 0.000 claims 4
- 240000004658 Medicago sativa Species 0.000 claims 1
- 230000008635 plant growth Effects 0.000 abstract description 6
- 239000003324 growth hormone secretagogue Substances 0.000 abstract description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- 239000000243 solution Substances 0.000 description 30
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical class NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 29
- 238000006243 chemical reaction Methods 0.000 description 26
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 25
- 239000003284 nod factor Substances 0.000 description 25
- 238000005160 1H NMR spectroscopy Methods 0.000 description 24
- 230000000694 effects Effects 0.000 description 24
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 239000012429 reaction media Substances 0.000 description 20
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 19
- 238000001819 mass spectrum Methods 0.000 description 19
- 238000012360 testing method Methods 0.000 description 19
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 17
- 235000000346 sugar Nutrition 0.000 description 17
- 229920005989 resin Polymers 0.000 description 16
- 239000011347 resin Substances 0.000 description 16
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- 239000007787 solid Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-MZCSYVLQSA-N CD3OD Substances [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 12
- 241000219823 Medicago Species 0.000 description 12
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 12
- 108090000623 proteins and genes Proteins 0.000 description 11
- 150000008163 sugars Chemical class 0.000 description 11
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 10
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 10
- 230000008878 coupling Effects 0.000 description 10
- 238000010168 coupling process Methods 0.000 description 10
- 238000005859 coupling reaction Methods 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 235000017557 sodium bicarbonate Nutrition 0.000 description 9
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 9
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
- 229940093499 ethyl acetate Drugs 0.000 description 8
- 235000019439 ethyl acetate Nutrition 0.000 description 8
- 150000002632 lipids Chemical group 0.000 description 8
- 239000002609 medium Substances 0.000 description 8
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 7
- 238000007792 addition Methods 0.000 description 7
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 210000004209 hair Anatomy 0.000 description 7
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- 235000011121 sodium hydroxide Nutrition 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 108700008625 Reporter Genes Proteins 0.000 description 6
- 238000007865 diluting Methods 0.000 description 6
- 238000010828 elution Methods 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
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- 239000000377 silicon dioxide Substances 0.000 description 6
- 229940083608 sodium hydroxide Drugs 0.000 description 6
- 241000219743 Lotus Species 0.000 description 5
- 241000219828 Medicago truncatula Species 0.000 description 5
- 235000006508 Nelumbo nucifera Nutrition 0.000 description 5
- 235000006510 Nelumbo pentapetala Nutrition 0.000 description 5
- 238000003556 assay Methods 0.000 description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 235000015320 potassium carbonate Nutrition 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 238000006467 substitution reaction Methods 0.000 description 5
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 4
- JOPLUKJEQHTEBL-FPLPWBNLSA-N 4-[(z)-undec-4-enoxy]benzoyl chloride Chemical compound CCCCCC\C=C/CCCOC1=CC=C(C(Cl)=O)C=C1 JOPLUKJEQHTEBL-FPLPWBNLSA-N 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
- 102000004190 Enzymes Human genes 0.000 description 4
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- 229940125797 compound 12 Drugs 0.000 description 4
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- MSWZFWKMSRAUBD-IVMDWMLBSA-N glucosamine group Chemical group OC1[C@H](N)[C@@H](O)[C@H](O)[C@H](O1)CO MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 4
- 108010003099 nodulin Proteins 0.000 description 4
- 238000005932 reductive alkylation reaction Methods 0.000 description 4
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- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- LTXNVHRZAODKMK-FPLPWBNLSA-N 3-[(z)-undec-4-enoxy]benzaldehyde Chemical compound CCCCCC\C=C/CCCOC1=CC=CC(C=O)=C1 LTXNVHRZAODKMK-FPLPWBNLSA-N 0.000 description 3
- OKNHHBZWZHSOCE-FPLPWBNLSA-N 3-[(z)-undec-4-enoxy]benzoyl chloride Chemical compound CCCCCC\C=C/CCCOC1=CC=CC(C(Cl)=O)=C1 OKNHHBZWZHSOCE-FPLPWBNLSA-N 0.000 description 3
- ULBAIKIGOIIOQL-UHFFFAOYSA-N 3-undecoxybenzoyl chloride Chemical compound CCCCCCCCCCCOC1=CC=CC(C(Cl)=O)=C1 ULBAIKIGOIIOQL-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
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- 101000603163 Medicago truncatula Early nodulin-11 Proteins 0.000 description 3
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- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 3
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- 229930014626 natural product Natural products 0.000 description 3
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- JXCKZXHCJOVIAV-UHFFFAOYSA-N 6-[(5-bromo-4-chloro-1h-indol-3-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid;cyclohexanamine Chemical compound [NH3+]C1CCCCC1.O1C(C([O-])=O)C(O)C(O)C(O)C1OC1=CNC2=CC=C(Br)C(Cl)=C12 JXCKZXHCJOVIAV-UHFFFAOYSA-N 0.000 description 2
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- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
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- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 238000004166 bioassay Methods 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
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- 239000012280 lithium aluminium hydride Substances 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- ZWDFYOKGVQZVFT-HJWRWDBZSA-N methyl 2-[(z)-undec-4-enoxy]benzoate Chemical compound CCCCCC\C=C/CCCOC1=CC=CC=C1C(=O)OC ZWDFYOKGVQZVFT-HJWRWDBZSA-N 0.000 description 2
- BUKCXTOARWMUNI-HJWRWDBZSA-N methyl 3-[(z)-undec-4-enoxy]benzoate Chemical compound CCCCCC\C=C/CCCOC1=CC=CC(C(=O)OC)=C1 BUKCXTOARWMUNI-HJWRWDBZSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic 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
- A01N43/14—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
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- Dentistry (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pretreatment Of Seeds And Plants (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Fertilizers (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR0315543A FR2864538B1 (fr) | 2003-12-30 | 2003-12-30 | Composes synthetiques utiles comme facteurs de nodulation des plantes legumineuses et procedes de preparation de tels composes |
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| OA13354A true OA13354A (en) | 2007-04-13 |
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| OA1200600218A OA13354A (en) | 2003-12-30 | 2004-12-22 | Synthetic compounds useful as nodulation agents ofleguminous plants and preparation processes thereof. |
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| EP (1) | EP1701967B1 (enExample) |
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| AU (1) | AU2004309089B2 (enExample) |
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| PL (1) | PL1701967T3 (enExample) |
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Families Citing this family (66)
| Publication number | Priority date | Publication date | Assignee | Title |
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| EP2348027B1 (en) | 2006-04-07 | 2013-10-23 | E. I. du Pont de Nemours and Company | Lipochitooligosaccharides |
| TWI462698B (zh) * | 2006-12-12 | 2014-12-01 | Bayer Cropscience Ag | 包括作為豆科植物生結瘤劑（ｎｏｄｕｌａｔｉｏｎ ａｇｅｎｔ）之合成化合物及殺昆蟲劑化合物之農藥組合物 |
| TWI421030B (zh) * | 2006-12-12 | 2014-01-01 | Bayer Cropscience Ag | 包括用作豆科植物生結瘤劑（ｎｏｄｕｌａｔｉｏｎ ａｇｅｎｔ）之合成化合物及殺真菌劑化合物之農藥組合物 |
| RU2508631C2 (ru) | 2007-01-09 | 2014-03-10 | Новозаймс Байолоджиклз Холдинг А/С | Композиции на основе комбинации липо-хитоолигосахарида для усиления роста и урожайности растений |
| BRPI0817934B1 (pt) * | 2007-10-16 | 2017-03-21 | Merck Patent Ges Mit Beschränkter Haftung | composição e métodos para melhorar sinergicamente o rendimento de plantação compreendendo combinação de genisteína, daidzeína e lipo-quitooligossacarídeo de rhizobium leguminosarum " |
| WO2010049751A1 (en) | 2008-10-29 | 2010-05-06 | Institut National De La Recherche Agronomique | Lipochitooligosaccharides stimulating arbuscular mycorrhizal symbiosis |
| BRPI1005810A2 (pt) * | 2009-04-28 | 2015-09-08 | Bayer Cropscience Ag | "composição, método para aprimorar o crescimento vegetal e/ou aumentar a produtividade de plantas ou colheitas e método para controlar de modo curativo ou preventivo fungos fitopatogênicos de colheitas e uso da composição" |
| WO2012120105A1 (en) | 2011-03-10 | 2012-09-13 | Bayer Cropscience Ag | Use of lipochito-oligosaccharide compounds for safeguarding seed safety of treated seeds |
| RU2611199C2 (ru) | 2011-03-31 | 2017-02-21 | Новозаймз Байолоджикалз, Инк | Конкурентоспособные и эффективные штаммы бактерий |
| EP3058826A1 (en) | 2011-09-08 | 2016-08-24 | Novozymes BioAG A/S | Seed treatment methods and compositions |
| PL2748123T3 (pl) | 2011-09-14 | 2024-05-13 | Novozymes Bioag A/S | Zastosowanie lipochito-oligosacharydów i/lub chito-oligosacharydów w kombinacji z mikroorganizmami solubilizującymi fosforany do poprawy wzrostu roślin |
| CA2849898C (en) | 2011-09-23 | 2020-10-27 | Novozymes Bioag A/S | Chitooligosaccharides and methods for use in enhancing plant growth |
| AU2012312006B2 (en) | 2011-09-23 | 2015-10-29 | Novozymes Bioag A/S | Chitooligosaccharides and methods for use in enhancing corn growth |
| CA2849889C (en) | 2011-09-23 | 2020-01-07 | Novozymes Biologicals, Inc. | Combinations of lipo-chitooligosaccharides and methods for use in enhancing plant growth |
| CN105746517A (zh) | 2011-09-23 | 2016-07-13 | 诺维信生物农业公司 | 用于增强大豆生长的壳寡糖和方法 |
| AU2012351899B2 (en) | 2011-12-16 | 2015-04-23 | Novozymes Bioag A/S | Bradyrhizobium strains |
| US20150011394A1 (en) | 2012-01-21 | 2015-01-08 | Bayer Intellectual Property Gmbh | Use of host defense inducers for controlling bacterial harmful organisms in useful plants |
| WO2013139949A1 (en) | 2012-03-23 | 2013-09-26 | Bayer Intellectual Property Gmbh | Compositions comprising a strigolactame compound for enhanced plant growth and yield |
| AR091104A1 (es) | 2012-05-22 | 2015-01-14 | Bayer Cropscience Ag | Combinaciones de compuestos activos que comprenden un derivado lipo-quitooligosacarido y un compuesto nematicida, insecticida o fungicida |
| FR2991682A1 (fr) * | 2012-06-12 | 2013-12-13 | Centre Nat Rech Scient | Procedes de preparation de lipochito-oligosaccharides et de leurs precurseurs |
| FR2994793A1 (fr) | 2012-08-30 | 2014-03-07 | Agronomique Inst Nat Rech | Utilisation d'un recepteur kinase a motifs lysm pour ameliorer la reponse des plantes aux lipochitooligosaccharides. |
| WO2014049546A2 (en) | 2012-09-27 | 2014-04-03 | Institut National De La Recherche Agronomique | Compositions and methods for enhancing plant growth and development |
| US9365464B2 (en) | 2012-11-16 | 2016-06-14 | Novozymes Bioag A/S | Microbial strains, compositions, and methods for increasing available phosphate for plants |
| US20160007600A1 (en) * | 2013-03-06 | 2016-01-14 | E.I. Du Pont De Nemours And Company | Synthetic lipochitooligosaccharide analogs for enhancing plant performance |
| US20160024108A1 (en) | 2013-03-12 | 2016-01-28 | Bayer Cropscience Aktiengesellschaft | Use of dithiine-tetracarboximides for controlling bacterial harmful organisms in useful plants |
| JP2016522678A (ja) | 2013-03-28 | 2016-08-04 | ノボザイムス バイオアーゲー アクティーゼルスカブ | 微生物の安定性を増大させる組成物と方法 |
| WO2015048627A1 (en) | 2013-09-30 | 2015-04-02 | Bayer Cropscience Lp, A Delaware Limited Partnership | Streptomyces microflavus strains and methods of their use for the treatment and prevention of citrus greening disease |
| UA119331C2 (uk) | 2013-11-08 | 2019-06-10 | Новозімес Біоаґ А/С | Композиції та способи для обробки від шкідників |
| AR098482A1 (es) | 2013-11-20 | 2016-06-01 | Novozymes Bioag As | Composiciones y métodos que comprenden chromobacterium para el control de nematodos e insectos pestes de plantas |
| WO2015112013A1 (en) * | 2014-01-24 | 2015-07-30 | Synaffix B.V. | Process for the attachment of a galnac moiety comprising a (hetero)aryl group to a glcnac moiety, and product obtained thereby |
| WO2015112016A1 (en) | 2014-01-24 | 2015-07-30 | Synaffix B.V. | Process for the cycloaddition of a halogenated 1,3-dipole compound with a (hetero)cycloalkyne |
| EP3097079B1 (en) | 2014-01-24 | 2021-05-12 | SynAffix B.V. | Process for the cycloaddition of a hetero(aryl) 1,3-dipole compound with a (hetero)cycloalkyne |
| WO2015134256A1 (en) | 2014-02-28 | 2015-09-11 | E. I. Du Pont De Nemours And Company | Combinatorial libraries |
| MX2016011413A (es) | 2014-03-05 | 2017-02-28 | Novozymes As | Formulaciones que comprenden xiloglucano polimérico como portador para agentes agronómicamente beneficiosos. |
| UA124920C2 (uk) | 2014-07-23 | 2021-12-15 | Новозімес Біоаґ А/С | Композиція, що містить ліпохітоолігосахарид і мікроорганізм, для підсилення росту рослин |
| RU2730863C2 (ru) | 2015-09-11 | 2020-08-26 | Новозимс Биоаг А/С | Стабильные композиции с инокулянтом и способы их получения |
| KR102867240B1 (ko) | 2015-12-28 | 2025-10-01 | 노보네시스 플랜트 바이오솔루션즈 에이/에스 | 안정한 접종제 조성물 및 그의 생성 방법 |
| EA201891171A1 (ru) | 2015-12-28 | 2018-11-30 | Новозимс Биоаг А/С | Стабильные композиции с инокулянтом и способы их получения |
| EP3462880A1 (en) | 2016-05-31 | 2019-04-10 | Novozymes BioAG A/S | Stable liquid inoculant compositions and coated plant propagation materials comprising same |
| WO2017210163A1 (en) | 2016-05-31 | 2017-12-07 | Novozymes Bioag A/S | Stable inoculant compositions and methods for producing same |
| WO2018118740A1 (en) | 2016-12-20 | 2018-06-28 | Novozymes Bioag A/S | Stable inoculant compositions and methods for producing same |
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| CA3048994A1 (en) | 2017-01-03 | 2018-07-12 | Monsanto Technology Llc | Microbial compositions and methods |
| CA3049029A1 (en) | 2017-01-04 | 2018-07-12 | Novozymes Bioag A/S | Bacillus isolates and uses thereof |
| UY37564A (es) | 2017-01-05 | 2018-07-31 | Novozymes Bioag As | Aislados de lysinibacillus y usos de los mismos |
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| US11716994B2 (en) | 2017-03-24 | 2023-08-08 | Novozymes Bioag A/S | Combinations of Yersinia entomophaga and pesticides or other substances |
| WO2018218016A1 (en) | 2017-05-26 | 2018-11-29 | Novozymes Bioag A/S | Stable inoculant compositions comprising paraffin oils/waxes |
| WO2018218008A1 (en) | 2017-05-26 | 2018-11-29 | Novozymes Bioag A/S | Stable liquid inoculant compositions comprising dodecane |
| CA3065297A1 (en) | 2017-05-26 | 2018-11-29 | Monsanto Technology Llc | Stable inoculant compositions comprising methylated plant oils |
| US20200288627A1 (en) | 2017-06-29 | 2020-09-17 | Monsanto Technology Llc | Seed treatment process for large liquid volumes |
| EP3681290A4 (en) | 2017-09-12 | 2021-06-16 | Monsanto Technology LLC | PROCESS FOR MANUFACTURING TREATED SEEDS |
| UA126979C2 (uk) | 2018-01-08 | 2023-03-01 | Новозімес Біоаґ А/С | Водна композиція, що містить солюбілізований ліпохітоолігосахарид |
| WO2019147660A1 (en) | 2018-01-23 | 2019-08-01 | Novozymes Bioag A/S | Method of enhancing seed germination under abiotic stress with chitin oligosaccharides |
| CA3097942A1 (en) | 2018-05-07 | 2019-11-14 | Novozymes Bioag A/S | Microbacterium isolates and uses thereof |
| US12052942B2 (en) | 2018-11-01 | 2024-08-06 | Monsanto Technology Llc | Seed treater |
| JP7513291B2 (ja) | 2019-06-24 | 2024-07-09 | 国立研究開発法人農業・食品産業技術総合研究機構 | エルウィニア属分離株およびその利用 |
| WO2020263812A1 (en) | 2019-06-24 | 2020-12-30 | Auburn University | A bacillus strain and methods of its use for plant growth promotion |
| EP3818829A3 (en) | 2019-10-16 | 2021-07-21 | Monsanto Technology LLC | Granular nematicide compositions |
| WO2021086695A1 (en) | 2019-10-29 | 2021-05-06 | Novozymes Bioag A/S | Microbacterium isolates and uses thereof |
| WO2021101937A1 (en) | 2019-11-20 | 2021-05-27 | Novozymes Bioag A/S | Pseudomonas isolates and uses thereof |
| BR112022009600A2 (pt) | 2019-11-22 | 2022-08-16 | Novozymes Bioag As | Paenibacillus peoriae fixador de nitrogênio isolado, cultura biologicamente pura de um paenibacillus peoriae fixador de nitrogênio, uso de um ou mais paenibacillus peoriae fixadores de nitrogênio e do consórcio microbiano sintético, método, composição inoculante e de sementes de ocorrência não natural, e, consórcio microbiano sintético |
| CN114075254B (zh) * | 2020-08-21 | 2024-01-30 | 佛山市海力盈生物科技有限公司 | 一类壳寡糖衍生物杀线剂及其制备方法和应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2660658A1 (fr) * | 1990-04-06 | 1991-10-11 | Centre Nat Rech Scient | Substances de structure oligosaccharidique propres a jouer le role de signaux symbiotiques plantes-specifiques, leurs procedes de production et leurs applications. |
| US5175149A (en) * | 1991-10-04 | 1992-12-29 | The University Of Tennessee Research Corporation | Pentasaccharide phytohormones and methods for their use |
| FR2692896B1 (fr) * | 1992-06-29 | 1994-09-09 | Institut Rech Agronomique | Signaux de nodulation de rhizobiaceae à large spectre d'hôte. |
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