ES2364556T3 - Compuestos sintéticos útiles como agentes de nodulación de plantas leguminosas y sus procedimientos de preparación. - Google Patents
Compuestos sintéticos útiles como agentes de nodulación de plantas leguminosas y sus procedimientos de preparación. Download PDFInfo
- Publication number
- ES2364556T3 ES2364556T3 ES04804487T ES04804487T ES2364556T3 ES 2364556 T3 ES2364556 T3 ES 2364556T3 ES 04804487 T ES04804487 T ES 04804487T ES 04804487 T ES04804487 T ES 04804487T ES 2364556 T3 ES2364556 T3 ES 2364556T3
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- represent
- substituent selected
- fucosyl
- independently
- 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.)
- Expired - Lifetime
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 128
- 230000024121 nodulation Effects 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 13
- 238000002360 preparation method Methods 0.000 title description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 318
- 125000001424 substituent group Chemical group 0.000 claims abstract description 188
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 128
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 121
- -1 methylfucosyl Chemical group 0.000 claims abstract description 120
- 125000002446 fucosyl group Chemical group C1([C@@H](O)[C@H](O)[C@H](O)[C@@H](O1)C)* 0.000 claims abstract description 87
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims abstract description 74
- 229910006069 SO3H Inorganic materials 0.000 claims abstract description 74
- 229910006145 SO3Li Inorganic materials 0.000 claims abstract description 74
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims abstract description 74
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 70
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 69
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 69
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 69
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 68
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 64
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 60
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 60
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 60
- 239000001301 oxygen Chemical group 0.000 claims abstract description 60
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 60
- 239000011593 sulfur Chemical group 0.000 claims abstract description 60
- 229910052717 sulfur Chemical group 0.000 claims abstract description 60
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims abstract description 58
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 53
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims abstract description 39
- 150000003839 salts Chemical class 0.000 claims abstract description 38
- 125000000089 arabinosyl group Chemical group C1([C@@H](O)[C@H](O)[C@H](O)CO1)* 0.000 claims abstract description 30
- 125000003118 aryl group Chemical group 0.000 claims abstract description 30
- 239000011734 sodium Chemical class 0.000 claims abstract description 29
- 125000004429 atom Chemical group 0.000 claims abstract description 28
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 22
- 150000002367 halogens Chemical class 0.000 claims abstract description 22
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 22
- 125000000732 arylene group Chemical group 0.000 claims abstract description 17
- 125000005549 heteroarylene group Chemical group 0.000 claims abstract description 17
- 125000004957 naphthylene group Chemical group 0.000 claims abstract description 15
- 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 abstract description 13
- 101100240526 Caenorhabditis elegans nhr-20 gene Proteins 0.000 claims abstract description 13
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 claims abstract description 13
- 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 abstract description 13
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical class 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 abstract description 13
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical class [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims abstract description 13
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 13
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical class [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims abstract description 13
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims abstract description 13
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 13
- 229910052744 lithium Inorganic materials 0.000 claims abstract description 13
- 229910052751 metal Inorganic materials 0.000 claims abstract description 13
- 239000002184 metal Chemical class 0.000 claims abstract description 13
- 229910052752 metalloid Inorganic materials 0.000 claims abstract description 13
- 150000002738 metalloids Chemical class 0.000 claims abstract description 13
- 230000003287 optical effect Effects 0.000 claims abstract description 13
- 239000011591 potassium Chemical class 0.000 claims abstract description 13
- 229910052700 potassium Inorganic materials 0.000 claims abstract description 13
- 229910052708 sodium Inorganic materials 0.000 claims abstract description 13
- 150000003462 sulfoxides Chemical class 0.000 claims abstract description 13
- 125000005207 tetraalkylammonium group Chemical class 0.000 claims abstract description 13
- 150000003457 sulfones Chemical class 0.000 claims abstract description 11
- 241000196324 Embryophyta Species 0.000 claims description 43
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 235000021374 legumes Nutrition 0.000 claims description 16
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 claims description 12
- 235000010469 Glycine max Nutrition 0.000 claims description 8
- 244000046052 Phaseolus vulgaris Species 0.000 claims description 8
- 235000010627 Phaseolus vulgaris Nutrition 0.000 claims description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 244000068988 Glycine max Species 0.000 claims description 6
- 240000004713 Pisum sativum Species 0.000 claims description 6
- 235000010582 Pisum sativum Nutrition 0.000 claims description 6
- 230000008635 plant growth Effects 0.000 claims description 5
- 241000219793 Trifolium Species 0.000 claims description 4
- 244000105624 Arachis hypogaea Species 0.000 claims description 3
- 235000020232 peanut Nutrition 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- 241000219745 Lupinus Species 0.000 claims description 2
- 150000001768 cations Chemical class 0.000 claims description 2
- 230000004936 stimulating effect Effects 0.000 claims description 2
- 125000001174 sulfone group Chemical class 0.000 claims description 2
- 240000004658 Medicago sativa Species 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 75
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 54
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 41
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- 239000000243 solution Substances 0.000 description 31
- 239000003284 nod factor Substances 0.000 description 30
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 29
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 28
- 239000012429 reaction media Substances 0.000 description 24
- 101150117004 atg18 gene Proteins 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- 230000000694 effects Effects 0.000 description 22
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 21
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 description 21
- 238000000132 electrospray ionisation Methods 0.000 description 20
- 238000001819 mass spectrum Methods 0.000 description 20
- 239000003921 oil Substances 0.000 description 20
- 239000000047 product Substances 0.000 description 19
- 235000000346 sugar Nutrition 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 229920005989 resin Polymers 0.000 description 17
- 239000011347 resin Substances 0.000 description 17
- 238000012360 testing method Methods 0.000 description 17
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 16
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 16
- 239000000203 mixture Substances 0.000 description 16
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 14
- 235000017557 sodium bicarbonate Nutrition 0.000 description 14
- 239000007787 solid Substances 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-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 12
- 150000003254 radicals Chemical class 0.000 description 12
- 150000008163 sugars Chemical class 0.000 description 12
- 125000003473 lipid group Chemical group 0.000 description 11
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 10
- 235000019439 ethyl acetate Nutrition 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- 150000003936 benzamides Chemical class 0.000 description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 9
- 230000008878 coupling Effects 0.000 description 9
- 238000010168 coupling process Methods 0.000 description 9
- 238000005859 coupling reaction Methods 0.000 description 9
- 239000002609 medium Substances 0.000 description 9
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 9
- 230000004044 response Effects 0.000 description 9
- 159000000000 sodium salts Chemical class 0.000 description 9
- 210000004209 hair Anatomy 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 241000215452 Lotus corniculatus Species 0.000 description 7
- 238000007792 addition Methods 0.000 description 7
- 239000000377 silicon dioxide Substances 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
- 229910052786 argon Inorganic materials 0.000 description 6
- 238000007865 diluting Methods 0.000 description 6
- 238000010828 elution Methods 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 101100537937 Caenorhabditis elegans arc-1 gene Proteins 0.000 description 5
- 125000003535 D-glucopyranosyl group Chemical group [H]OC([H])([H])[C@@]1([H])OC([H])(*)[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H] 0.000 description 5
- 241000219828 Medicago truncatula Species 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 235000015320 potassium carbonate Nutrition 0.000 description 5
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 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
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 229920002101 Chitin Polymers 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
- 108090000790 Enzymes Proteins 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 229940125797 compound 12 Drugs 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 230000004927 fusion Effects 0.000 description 4
- 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
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 4
- 239000000463 material Substances 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
- 239000000843 powder Substances 0.000 description 4
- 102000004169 proteins and genes Human genes 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- DVNSVUYFHBIVPI-FPLPWBNLSA-N 2-[(z)-undec-4-enoxy]benzoyl chloride Chemical compound CCCCCC\C=C/CCCOC1=CC=CC=C1C(Cl)=O DVNSVUYFHBIVPI-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
- 229920001817 Agar Polymers 0.000 description 3
- 101000603163 Medicago truncatula Early nodulin-11 Proteins 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 230000009418 agronomic effect Effects 0.000 description 3
- 238000003556 assay Methods 0.000 description 3
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 3
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000001963 growth medium Substances 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 230000006698 induction Effects 0.000 description 3
- WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 3
- 229930014626 natural product Natural products 0.000 description 3
- 150000002482 oligosaccharides Polymers 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 238000005932 reductive alkylation reaction Methods 0.000 description 3
- 230000001850 reproductive effect Effects 0.000 description 3
- 238000007127 saponification reaction Methods 0.000 description 3
- 230000031068 symbiosis, encompassing mutualism through parasitism Effects 0.000 description 3
- 230000035897 transcription Effects 0.000 description 3
- 238000013518 transcription Methods 0.000 description 3
- IKPSIIAXIDAQLG-UHFFFAOYSA-N 1-bromoundecane Chemical compound CCCCCCCCCCCBr IKPSIIAXIDAQLG-UHFFFAOYSA-N 0.000 description 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 244000045195 Cicer arietinum Species 0.000 description 2
- 235000010523 Cicer arietinum Nutrition 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 101150019433 DMI1 gene Proteins 0.000 description 2
- 101150093050 ENOD11 gene Proteins 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- 230000006181 N-acylation Effects 0.000 description 2
- 108091028043 Nucleic acid sequence Proteins 0.000 description 2
- 241000589180 Rhizobium Species 0.000 description 2
- 241000589196 Sinorhizobium meliloti Species 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 150000001263 acyl chlorides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 238000011953 bioanalysis Methods 0.000 description 2
- 230000004071 biological effect Effects 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 244000038559 crop plants Species 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 description 2
- 208000015181 infectious disease Diseases 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
- YKUCHDXIBAQWSF-UHFFFAOYSA-N methyl 3-hydroxybenzoate Chemical compound COC(=O)C1=CC=CC(O)=C1 YKUCHDXIBAQWSF-UHFFFAOYSA-N 0.000 description 2
- 229960001047 methyl salicylate Drugs 0.000 description 2
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 2
- 230000035772 mutation Effects 0.000 description 2
- 229920001542 oligosaccharide Polymers 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000006722 reduction reaction Methods 0.000 description 2
- 239000012508 resin bead Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 238000010361 transduction Methods 0.000 description 2
- 230000026683 transduction Effects 0.000 description 2
- 230000009261 transgenic effect Effects 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 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 1
- 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 1
- 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 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 108010082495 Dietary Plant Proteins Proteins 0.000 description 1
- 241000218922 Magnoliophyta Species 0.000 description 1
- 101100387458 Medicago truncatula DMI1 gene Proteins 0.000 description 1
- 101100516767 Medicago truncatula ENOD11 gene Proteins 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- 240000002853 Nelumbo nucifera Species 0.000 description 1
- 235000006508 Nelumbo nucifera Nutrition 0.000 description 1
- 101100097982 Pisum sativum SYM8 gene Proteins 0.000 description 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- UWHZIFQPPBDJPM-FPLPWBNLSA-M Vaccenic acid Natural products CCCCCC\C=C/CCCCCCCCCC([O-])=O UWHZIFQPPBDJPM-FPLPWBNLSA-M 0.000 description 1
- 235000021322 Vaccenic acid Nutrition 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000003213 activating effect Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000001345 alkine derivatives Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000003816 axenic effect Effects 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- MSWZFWKMSRAUBD-UHFFFAOYSA-N beta-D-galactosamine Natural products NC1C(O)OC(CO)C(O)C1O MSWZFWKMSRAUBD-UHFFFAOYSA-N 0.000 description 1
- 230000031018 biological processes and functions Effects 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 238000000339 bright-field microscopy Methods 0.000 description 1
- 229920001429 chelating resin Polymers 0.000 description 1
- 238000000451 chemical ionisation Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000005352 clarification Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 229940125773 compound 10 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 238000003795 desorption Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000003113 dilution method Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- INCWELKXTZCRSA-UHFFFAOYSA-N ethyl acetate;methanol;hydrate Chemical compound O.OC.CCOC(C)=O INCWELKXTZCRSA-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229930003935 flavonoid Natural products 0.000 description 1
- 150000002215 flavonoids Chemical class 0.000 description 1
- 235000017173 flavonoids Nutrition 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000004459 forage Substances 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000010353 genetic engineering Methods 0.000 description 1
- 125000005640 glucopyranosyl group Chemical group 0.000 description 1
- 229960002442 glucosamine Drugs 0.000 description 1
- 229930182480 glucuronide Natural products 0.000 description 1
- 150000008134 glucuronides Chemical class 0.000 description 1
- ZEKANFGSDXODPD-UHFFFAOYSA-N glyphosate-isopropylammonium Chemical compound CC(C)N.OC(=O)CNCP(O)(O)=O ZEKANFGSDXODPD-UHFFFAOYSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 239000003324 growth hormone secretagogue Substances 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229940120152 methyl 3-hydroxybenzoate Drugs 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
- CXKWCBBOMKCUKX-UHFFFAOYSA-M methylene blue Chemical compound [Cl-].C1=CC(N(C)C)=CC2=[S+]C3=CC(N(C)C)=CC=C3N=C21 CXKWCBBOMKCUKX-UHFFFAOYSA-M 0.000 description 1
- 229960000907 methylthioninium chloride Drugs 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 239000000618 nitrogen fertilizer Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 230000008121 plant development Effects 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 235000021251 pulses Nutrition 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 230000003252 repetitive effect Effects 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000010187 selection method Methods 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
- UWHZIFQPPBDJPM-BQYQJAHWSA-N trans-vaccenic acid Chemical compound CCCCCC\C=C\CCCCCCCCCC(O)=O UWHZIFQPPBDJPM-BQYQJAHWSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 241001478887 unidentified soil bacteria Species 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- 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)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pretreatment Of Seeds And Plants (AREA)
- Fertilizers (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Steroid Compounds (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
Applications Claiming Priority (2)
| 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 |
| FR0315543 | 2003-12-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2364556T3 true ES2364556T3 (es) | 2011-09-06 |
Family
ID=34639685
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES04804487T Expired - Lifetime ES2364556T3 (es) | 2003-12-30 | 2004-12-22 | Compuestos sintéticos útiles como agentes de nodulación de plantas leguminosas y sus procedimientos de preparación. |
Country Status (25)
| Country | Link |
|---|---|
| US (3) | US7619076B2 (https=) |
| EP (1) | EP1701967B1 (https=) |
| JP (1) | JP5031376B2 (https=) |
| KR (1) | KR101127785B1 (https=) |
| CN (1) | CN100549020C (https=) |
| AP (1) | AP2328A (https=) |
| AR (2) | AR047174A1 (https=) |
| AT (1) | ATE504593T1 (https=) |
| AU (1) | AU2004309089B2 (https=) |
| BR (1) | BRPI0417892B1 (https=) |
| CA (1) | CA2540074C (https=) |
| DE (1) | DE602004032175D1 (https=) |
| EA (1) | EA009557B1 (https=) |
| ES (1) | ES2364556T3 (https=) |
| FR (1) | FR2864538B1 (https=) |
| IL (1) | IL175658A (https=) |
| IN (1) | IN2006DE01668A (https=) |
| MA (1) | MA28296A1 (https=) |
| MX (1) | MX258070B (https=) |
| NZ (1) | NZ546188A (https=) |
| OA (1) | OA13354A (https=) |
| PL (1) | PL1701967T3 (https=) |
| PT (1) | PT1701967E (https=) |
| WO (1) | WO2005063784A1 (https=) |
| ZA (1) | ZA200605258B (https=) |
Families Citing this family (66)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2644172A1 (en) | 2006-04-07 | 2007-10-18 | E.I. Du Pont De Nemours And Company | Processes for chemical synthesis of lipochitooligosaccharides |
| 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 |
| 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 |
| US8357631B2 (en) | 2007-01-09 | 2013-01-22 | Novozymes Bioag, Inc. | Lipo-chitooligosaccharide combination compositions for enhanced plant growth and yield |
| WO2009049747A2 (en) * | 2007-10-16 | 2009-04-23 | Merck Patent Gmbh | Lipo-chitooligosaccharide and flavonoid combination for enhanced plant growth and yield |
| WO2010049751A1 (en) | 2008-10-29 | 2010-05-06 | Institut National De La Recherche Agronomique | Lipochitooligosaccharides stimulating arbuscular mycorrhizal symbiosis |
| WO2010125065A2 (en) * | 2009-04-28 | 2010-11-04 | Bayer Cropscience Ag | Compositions comprising a strigolactone compound and a chito-oligosaccharide compound for enhanced plant growth and yield |
| EP2683239A1 (en) * | 2011-03-10 | 2014-01-15 | Bayer Intellectual Property GmbH | Use of lipochito-oligosaccharide compounds for safeguarding seed safety of treated seeds |
| WO2012135704A1 (en) | 2011-03-31 | 2012-10-04 | Novozymes Biologicials, Inc | Competitive and effective bradyrhizobium japonicum strains |
| AR090026A1 (es) | 2011-09-08 | 2014-10-15 | Novozymes Bioag As | Metodos y composiciones para tratamiento de semillas |
| ES2970761T3 (es) | 2011-09-14 | 2024-05-30 | Novozymes Bioag As | Uso de lipoquitooligosacáridos y/o quitooligosacáridos en combinación con microorganismos solubilizadores de fosfato para potenciar el crecimiento de las plantas |
| RU2564844C1 (ru) | 2011-09-23 | 2015-10-10 | Новозимс Биоаг А/С | Хитоолигосахариды и способы их применения для усиления роста растений |
| UA123664C2 (uk) | 2011-09-23 | 2021-05-12 | Новозаймс Біоаг А/С | Комбінації ліпохітоолігосахаридів і способи для застосування при стимулюванні росту рослин |
| CA2849899A1 (en) | 2011-09-23 | 2013-03-28 | Novozymes Bioag A/S | Chitooligosaccharides and methods for use in enhancing soybean growth |
| AU2012312006B2 (en) | 2011-09-23 | 2015-10-29 | Novozymes Bioag A/S | Chitooligosaccharides and methods for use in enhancing corn growth |
| RU2646138C1 (ru) | 2011-12-16 | 2018-03-01 | Новозимс Биоаг А/С | Способ обработки семени растения |
| WO2013107785A1 (en) | 2012-01-21 | 2013-07-25 | 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 |
| CA2904328A1 (en) * | 2013-03-06 | 2014-09-12 | 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 |
| WO2014160827A1 (en) | 2013-03-28 | 2014-10-02 | Novozymes Bioag A/S | Compositions and methods for enhancing microbial stability |
| 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 |
| WO2015077278A1 (en) | 2013-11-20 | 2015-05-28 | Novozymes Bioag A/S | Compositions and methods comprising chromobacterium for controlling plant nematode pests and plant insect pests |
| CN106660967A (zh) | 2014-01-24 | 2017-05-10 | 西纳福克斯股份有限公司 | (杂)芳基1，3‑偶极化合物与(杂)环炔的环加成方法 |
| 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 |
| WO2015134256A1 (en) | 2014-02-28 | 2015-09-11 | E. I. Du Pont De Nemours And Company | Combinatorial libraries |
| BR112016020374A2 (pt) | 2014-03-05 | 2018-01-23 | Novozymes As | formulação, e, métodos para potenciar o crescimento de plantas e para formular um ou mais agentes agricolamente benéficos |
| BR112017000877B1 (pt) | 2014-07-23 | 2020-04-07 | Novozymes Bioag As | método para intensificação sinérgica do crescimento de uma planta ou parte de planta |
| US11472981B2 (en) | 2015-09-11 | 2022-10-18 | Novozymes Bioag A/S | Stable inoculant compositions and methods for producing same |
| JP2019503714A (ja) | 2015-12-28 | 2019-02-14 | ノボザイムス バイオアーゲー アクティーゼルスカブ | 安定した接種組成物およびその製造方法 |
| WO2017116837A1 (en) | 2015-12-28 | 2017-07-06 | Novozymes Bioag A/S | Stable inoculant compositions and methods for producing same |
| US20200315183A1 (en) | 2016-05-31 | 2020-10-08 | Novozymes A/S | Stable inoculant compositions and methods for producing same |
| CA3025912A1 (en) | 2016-05-31 | 2017-12-07 | Novozymes Bioag A/S | Stable liquid inoculant compositions and coated plant propagation materials comprising same |
| BR112019012319A2 (pt) | 2016-12-20 | 2019-11-19 | Novozymes Bioag As | composição inoculante, métodos, material de propagação de planta revestido, e, kit. |
| US20190320661A1 (en) | 2017-01-03 | 2019-10-24 | Monsanto Technology, Llc | Microbial compositions and methods |
| EP3565396A4 (en) | 2017-01-03 | 2020-06-24 | Monsanto Technology LLC | MICROBIAL COMPOSITIONS AND METHODS |
| UY37563A (es) | 2017-01-04 | 2018-07-31 | Novozymes Bioag As | Aislados de bacillus y usos de los mismos |
| US20190345572A1 (en) | 2017-01-05 | 2019-11-14 | Novozymes Bioag A/S | Lysinibacillus isolates and uses thereof |
| US11089776B2 (en) | 2017-02-28 | 2021-08-17 | Monsanto Technology Llc | Containerized liquid formulations |
| WO2018159393A1 (ja) * | 2017-03-01 | 2018-09-07 | 花王株式会社 | マメ科植物生育促進剤 |
| CA3056903A1 (en) | 2017-03-24 | 2018-09-27 | Novozymes Bioag A/S | Combinations of yersinia entomophaga and pesticides or other substances |
| PL3631019T3 (pl) | 2017-05-26 | 2024-03-11 | Novozymes Bioag A/S | Stabilne kompozycje inokulacyjne zawierające oleje/woski parafinowe |
| CA3065297A1 (en) | 2017-05-26 | 2018-11-29 | Monsanto Technology Llc | Stable inoculant compositions comprising methylated plant oils |
| CA3064437A1 (en) | 2017-05-26 | 2018-11-29 | Novozymes Bioag A/S | Stable liquid inoculant compositions comprising dodecane |
| WO2019006226A1 (en) | 2017-06-29 | 2019-01-03 | Monsanto Technology Llc | METHOD FOR TREATING SEEDS FOR LARGE VOLUMES OF LIQUID |
| AR113018A1 (es) | 2017-09-12 | 2020-01-15 | Monsanto Technology Llc | Procesos para la preparación de semillas tratadas |
| CA3085953A1 (en) | 2018-01-08 | 2019-07-11 | Novozymes Bioag A/S | Aqueous compositions comprising solubilzed lipo-chitooligosaccharides |
| WO2019147660A1 (en) | 2018-01-23 | 2019-08-01 | Novozymes Bioag A/S | Method of enhancing seed germination under abiotic stress with chitin oligosaccharides |
| AU2019266155A1 (en) | 2018-05-07 | 2020-11-05 | Novozymes Bioag A/S | Microbacterium isolates and uses thereof |
| WO2020092866A1 (en) | 2018-11-01 | 2020-05-07 | 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 |
| EP3986138B1 (en) | 2019-06-24 | 2026-01-28 | 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 |
| WO2022125639A1 (en) | 2020-12-08 | 2022-06-16 | Monsanto Technology Llc | Modified plant-associated bacteria and methods of their use |
| CN119859078B (zh) * | 2025-01-23 | 2025-07-18 | 江西瑞博特生物科技有限公司 | 一种氨基酸硒叶面肥及其制备方法 |
Family Cites Families (3)
| 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. |
-
2003
- 2003-12-30 FR FR0315543A patent/FR2864538B1/fr not_active Expired - Fee Related
-
2004
- 2004-12-22 KR KR1020067012968A patent/KR101127785B1/ko not_active Expired - Fee Related
- 2004-12-22 CA CA2540074A patent/CA2540074C/en not_active Expired - Lifetime
- 2004-12-22 AU AU2004309089A patent/AU2004309089B2/en not_active Ceased
- 2004-12-22 CN CNB2004800339994A patent/CN100549020C/zh not_active Expired - Fee Related
- 2004-12-22 PL PL04804487T patent/PL1701967T3/pl unknown
- 2004-12-22 AT AT04804487T patent/ATE504593T1/de not_active IP Right Cessation
- 2004-12-22 MX MXPA06007465 patent/MX258070B/es active IP Right Grant
- 2004-12-22 PT PT04804487T patent/PT1701967E/pt unknown
- 2004-12-22 EP EP04804487A patent/EP1701967B1/en not_active Expired - Lifetime
- 2004-12-22 JP JP2006546134A patent/JP5031376B2/ja not_active Expired - Fee Related
- 2004-12-22 US US10/583,567 patent/US7619076B2/en not_active Expired - Lifetime
- 2004-12-22 BR BRPI0417892-0A patent/BRPI0417892B1/pt not_active IP Right Cessation
- 2004-12-22 DE DE602004032175T patent/DE602004032175D1/de not_active Expired - Lifetime
- 2004-12-22 NZ NZ546188A patent/NZ546188A/en not_active IP Right Cessation
- 2004-12-22 OA OA1200600218A patent/OA13354A/en unknown
- 2004-12-22 ES ES04804487T patent/ES2364556T3/es not_active Expired - Lifetime
- 2004-12-22 AP AP2006003581A patent/AP2328A/xx active
- 2004-12-22 WO PCT/EP2004/014909 patent/WO2005063784A1/en not_active Ceased
- 2004-12-22 EA EA200601260A patent/EA009557B1/ru not_active IP Right Cessation
- 2004-12-29 AR ARP040104942A patent/AR047174A1/es active IP Right Grant
-
2006
- 2006-03-28 IN IN1668DE2006 patent/IN2006DE01668A/en unknown
- 2006-05-16 IL IL175658A patent/IL175658A/en active IP Right Grant
- 2006-06-26 ZA ZA200605258A patent/ZA200605258B/en unknown
- 2006-07-14 MA MA29189A patent/MA28296A1/fr unknown
-
2009
- 2009-09-30 US US12/587,060 patent/US8013132B2/en not_active Expired - Lifetime
-
2011
- 2011-07-28 US US13/193,505 patent/US8198420B2/en not_active Expired - Fee Related
-
2016
- 2016-02-25 AR ARP160100493A patent/AR103791A2/es unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| ES2364556T3 (es) | Compuestos sintéticos útiles como agentes de nodulación de plantas leguminosas y sus procedimientos de preparación. | |
| EP0847241B1 (en) | Influencing the activity of plant growth regulators | |
| ES2856864T3 (es) | Lipo-quito-oligosacáridos que estimulan la simbiosis micorrícica arbuscular | |
| EA018062B1 (ru) | Пестицидная композиция, содержащая синтетическое соединение, полезное в качестве агента образования клубней бобовых растений, и фунгицидное соединение | |
| BR122016008019B1 (pt) | composição, métodos para controlar insetos e aumentar o rendimento de safras e usos da composição | |
| US20200178534A1 (en) | Induction of floral development in plants | |
| US5032611A (en) | Lactone compound of agricultural utility | |
| US20030027722A1 (en) | Influencing the activity of plant growth regulators | |
| CN118420691B (zh) | 含硝基苄氧羰基酯阿维菌素衍生物及其合成方法和用途 | |
| EP0576116A1 (en) | Physiologically active substances of plant, process for the preparation thereof, and utilities thereof | |
| RU1813375C (ru) | Способ индукции апогамии колосовых культур | |
| CN115286724A (zh) | 植物免疫激活剂葡聚六糖的高效合成方法 | |
| CN114206831A (zh) | 生长素类似物的缀合物 | |
| Wardell | FLORAL TRANSFORMATION OF VEGETATIVE PLANTS BY SOLUTIONS CONTAINING DEOXYRIBONUCLEIC ACID EXTRACTED FROM STEMS IN A FLORAL STATE | |
| JP2006316014A (ja) | ４−クロロインドール−３−酢酸の乳酸誘導体 | |
| JPH02299595A (ja) | 体細胞不定胚によるブラシノステロイドの生産方法 | |
| BR102013010176A2 (pt) | Otimização de processo de obtenção de acil-homosserina lactonas e desenvolvimento de produto regulador de crescimento para cana-de-açúcar |