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 PDF

Info

Publication number: OA13354A
Authority: OA; OAPI
Prior art keywords: alkyl; represent; fucosyl; chosen; substituent chosen
Prior art date: 2003-12-30

Application number

OA1200600218A

Other languages

English (en)

Inventor

Jean-Marie Beau

Jean Denarie

Alfred Greiner

Nathalie Grenaouillat

Fabienne Maillet

Boris Vauzeilles

Original Assignee

Bayer Cropsciensce Sa

Agronomique Inst Nat Rech

Centre Nat Rech Scient

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2003-12-30

Filing date

2004-12-22

Publication date

2007-04-13

2004-12-22 Application filed by Bayer Cropsciensce Sa, Agronomique Inst Nat Rech, Centre Nat Rech Scient filed Critical Bayer Cropsciensce Sa

2007-04-13 Publication of OA13354A publication Critical patent/OA13354A/en

Links

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
230000004044 response Effects 0.000 description 7
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
229910002027 silica gel Inorganic materials 0.000 description 6
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
108090000790 Enzymes Proteins 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
229910052786 argon Inorganic materials 0.000 description 4
229940125797 compound 12 Drugs 0.000 description 4
238000001704 evaporation Methods 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
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
238000007127 saponification reaction Methods 0.000 description 4
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
102000053187 Glucuronidase Human genes 0.000 description 3
108010060309 Glucuronidase Proteins 0.000 description 3
101000603163 Medicago truncatula Early nodulin-11 Proteins 0.000 description 3
230000006181 N-acylation Effects 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 3
244000038559 crop plants Species 0.000 description 3
150000002148 esters Chemical class 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
125000004430 oxygen atom Chemical group O* 0.000 description 3
102000004169 proteins and genes Human genes 0.000 description 3
238000000746 purification Methods 0.000 description 3
VQKHMHRRABVJHV-FPLPWBNLSA-N (z)-1-iodoundec-4-ene Chemical compound CCCCCC\C=C/CCCI VQKHMHRRABVJHV-FPLPWBNLSA-N 0.000 description 2
IKPSIIAXIDAQLG-UHFFFAOYSA-N 1-bromoundecane Chemical compound CCCCCCCCCCCBr IKPSIIAXIDAQLG-UHFFFAOYSA-N 0.000 description 2
VEXHETMAVWQICS-FPLPWBNLSA-N 2-[(z)-undec-4-enoxy]benzoic acid Chemical compound CCCCCC\C=C/CCCOC1=CC=CC=C1C(O)=O VEXHETMAVWQICS-FPLPWBNLSA-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
PMMURAAUARKVCB-CERMHHMHSA-N 2-deoxy-D-glucopyranose Chemical compound OC[C@H]1OC(O)C[C@@H](O)[C@@H]1O PMMURAAUARKVCB-CERMHHMHSA-N 0.000 description 2
TZLITNXFCBFHAS-FPLPWBNLSA-N 3-[(z)-undec-4-enoxy]benzoic acid Chemical compound CCCCCC\C=C/CCCOC1=CC=CC(C(O)=O)=C1 TZLITNXFCBFHAS-FPLPWBNLSA-N 0.000 description 2
MYJODYRKYSJQQP-UHFFFAOYSA-N 3-undec-4-ynoxybenzoic acid Chemical compound CCCCCCC#CCCCOC1=CC=CC(C(O)=O)=C1 MYJODYRKYSJQQP-UHFFFAOYSA-N 0.000 description 2
YGOQPLFKICEHLC-UHFFFAOYSA-N 3-undecoxybenzoic acid Chemical compound CCCCCCCCCCCOC1=CC=CC(C(O)=O)=C1 YGOQPLFKICEHLC-UHFFFAOYSA-N 0.000 description 2
WUBQDMDMSJTSEE-FPLPWBNLSA-N 4-[(z)-undec-4-enoxy]benzoic acid Chemical compound CCCCCC\C=C/CCCOC1=CC=C(C(O)=O)C=C1 WUBQDMDMSJTSEE-FPLPWBNLSA-N 0.000 description 2
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
229920001817 Agar Polymers 0.000 description 2
229920002101 Chitin Polymers 0.000 description 2
235000010523 Cicer arietinum Nutrition 0.000 description 2
244000045195 Cicer arietinum Species 0.000 description 2
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241000215452 Lotus corniculatus Species 0.000 description 2
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241000589196 Sinorhizobium meliloti Species 0.000 description 2
241000219793 Trifolium Species 0.000 description 2
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235000010749 Vicia faba Nutrition 0.000 description 2
235000002098 Vicia faba var. major Nutrition 0.000 description 2
VKXQIWJVXKWUPL-FPLPWBNLSA-N [3-[(z)-undec-4-enoxy]phenyl]methanol Chemical compound CCCCCC\C=C/CCCOC1=CC=CC(CO)=C1 VKXQIWJVXKWUPL-FPLPWBNLSA-N 0.000 description 2
238000010521 absorption reaction Methods 0.000 description 2
238000006640 acetylation reaction Methods 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
230000009471 action Effects 0.000 description 2
150000001263 acyl chlorides Chemical class 0.000 description 2
239000008272 agar Substances 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
150000003936 benzamides Chemical class 0.000 description 2
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
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
150000001805 chlorine compounds Chemical class 0.000 description 2
238000000921 elemental analysis Methods 0.000 description 2
239000004459 forage Substances 0.000 description 2
239000001963 growth medium Substances 0.000 description 2
238000003306 harvesting Methods 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
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
YKUCHDXIBAQWSF-UHFFFAOYSA-N methyl 3-hydroxybenzoate Chemical compound COC(=O)C1=CC=CC(O)=C1 YKUCHDXIBAQWSF-UHFFFAOYSA-N 0.000 description 2
UBLUDDJEQFMALB-UHFFFAOYSA-N methyl 3-undec-4-ynoxybenzoate Chemical compound CCCCCCC#CCCCOC1=CC=CC(C(=O)OC)=C1 UBLUDDJEQFMALB-UHFFFAOYSA-N 0.000 description 2
SDUDWWGOSMCPBN-UHFFFAOYSA-N methyl 3-undecoxybenzoate Chemical compound CCCCCCCCCCCOC1=CC=CC(C(=O)OC)=C1 SDUDWWGOSMCPBN-UHFFFAOYSA-N 0.000 description 2
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201000002569 3-methylglutaconic aciduria type 5 Diseases 0.000 description 1
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DHJFFLKPAYHPHU-BYNIDDHOSA-N 5-bromo-4-chloro-3-indolyl beta-D-glucuronide Chemical compound O1[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1OC1=CNC2=CC=C(Br)C(Cl)=C12 DHJFFLKPAYHPHU-BYNIDDHOSA-N 0.000 description 1
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UWHZIFQPPBDJPM-FPLPWBNLSA-M Vaccenic acid Natural products CCCCCC\C=C/CCCCCCCCCC([O-])=O UWHZIFQPPBDJPM-FPLPWBNLSA-M 0.000 description 1
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INCWELKXTZCRSA-UHFFFAOYSA-N ethyl acetate;methanol;hydrate Chemical compound O.OC.CCOC(C)=O INCWELKXTZCRSA-UHFFFAOYSA-N 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
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ZEKANFGSDXODPD-UHFFFAOYSA-N glyphosate-isopropylammonium Chemical compound CC(C)N.OC(=O)CNCP(O)(O)=O ZEKANFGSDXODPD-UHFFFAOYSA-N 0.000 description 1
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239000003630 growth substance Substances 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
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GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
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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
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FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
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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)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Biotechnology (AREA)
Biochemistry (AREA)
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)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Pretreatment Of Seeds And Plants (AREA)
Fertilizers (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Polysaccharides And Polysaccharide Derivatives (AREA)
Steroid Compounds (AREA)

OA1200600218A 2003-12-30 2004-12-22 Synthetic compounds useful as nodulation agents ofleguminous plants and preparation processes thereof. OA13354A (en)

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

Publications (1)

Publication Number	Publication Date
OA13354A true OA13354A (en)	2007-04-13

Family

ID=34639685

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA1200600218A OA13354A (en)	2003-12-30	2004-12-22	Synthetic compounds useful as nodulation agents ofleguminous plants and preparation processes thereof.

Country Status (25)

Country	Link
US (3)	US7619076B2 (fr)
EP (1)	EP1701967B1 (fr)
JP (1)	JP5031376B2 (fr)
KR (1)	KR101127785B1 (fr)
CN (1)	CN100549020C (fr)
AP (1)	AP2328A (fr)
AR (2)	AR047174A1 (fr)
AT (1)	ATE504593T1 (fr)
AU (1)	AU2004309089B2 (fr)
BR (1)	BRPI0417892B1 (fr)
CA (1)	CA2540074C (fr)
DE (1)	DE602004032175D1 (fr)
EA (1)	EA009557B1 (fr)
ES (1)	ES2364556T3 (fr)
FR (1)	FR2864538B1 (fr)
IL (1)	IL175658A (fr)
IN (1)	IN2006DE01668A (fr)
MA (1)	MA28296A1 (fr)
MX (1)	MX258070B (fr)
NZ (1)	NZ546188A (fr)
OA (1)	OA13354A (fr)
PL (1)	PL1701967T3 (fr)
PT (1)	PT1701967E (fr)
WO (1)	WO2005063784A1 (fr)
ZA (1)	ZA200605258B (fr)

Families Citing this family (66)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP2348028B1 (fr)	2006-04-07	2012-08-22	E. I. du Pont de Nemours and Company	Procédés de synthèse chimique de lipochitooligosaccharides
TWI462698B (zh) *	2006-12-12	2014-12-01	Bayer Cropscience Ag	包括作為豆科植物生結瘤劑（ｎｏｄｕｌａｔｉｏｎａｇｅｎｔ）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（ｎｏｄｕｌａｔｉｏｎａｇｅｎｔ）之合成化合物及殺真菌劑化合物之農藥組合物
MX336621B (es)	2007-01-09	2016-01-26	Merck Patent Gmbh	Composiciones de combinacion de lipoquitooligosacaridos para crecimiento y rendimiento de plantas mejoradas.
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 (fr)	2008-10-29	2010-05-06	Institut National De La Recherche Agronomique	Lipochitooligosaccharides stimulant la symbiose mycorhizienne arbusculaire
WO2010125065A2 (fr) *	2009-04-28	2010-11-04	Bayer Cropscience Ag	Compositions comprenant un composé strigolactone et un composé chito-oligosaccharide pour une croissance végétale et un rendement végétal accrus
US20130345058A1 (en) *	2011-03-10	2013-12-26	Wolfram Andersch	Use of lipochito-oligosaccharide compounds for safeguarding seed safety of treated seeds
EP2690959B1 (fr)	2011-03-31	2016-03-23	Novozymes Biologicals, Inc.	Souches compétitives et efficaces de bradyrhizobium japonicum
AR090026A1 (es)	2011-09-08	2014-10-15	Novozymes Bioag As	Metodos y composiciones para tratamiento de semillas
EP2748123B1 (fr)	2011-09-14	2023-11-08	Novozymes Bioag A/S	Utilisation de lipochito-oligosaccharides et/ou de chito-oligosaccharides en association avec des micro-organismes solubilisant les phosphates pour améliorer la croissance des plantes
EP2747568B1 (fr)	2011-09-23	2019-05-22	Novozymes Bioag A/S	Combinaisons de lipo-chito-oligosaccharides et leurs méthodes d'utilisation pour améliorer la croissance de plantes
MX2014003411A (es)	2011-09-23	2015-03-19	Novozymes Bioag As	Quitooligosacaridos y metodos para el uso en el mejoramiento del crecimiento del maiz.
CA2849899A1 (fr)	2011-09-23	2013-03-28	Novozymes Bioag A/S	Chito-oligosaccharides et leurs methodes d'utilisation pour ameliorer la croissance du soja
UA114299C2 (uk)	2011-09-23	2017-05-25	Новозаймс Біоаг А/С	Хітоолігосахариди та способи застосування при стимулюванні росту рослин
CN104093829B (zh)	2011-12-16	2017-08-15	诺维信生物农业公司	慢生根瘤菌菌株
MX2014008358A (es)	2012-01-21	2014-10-14	Bayer Ip Gmbh	Uso de inductores de la defensa del huesped para controlar organismos bacterianos perjudicales en plantas utiles.
WO2013139949A1 (fr)	2012-03-23	2013-09-26	Bayer Intellectual Property Gmbh	Compositions comprenant un composé de strigolactame pour la croissance et le rendement accrus de plantes
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 (fr)	2012-09-27	2014-04-03	Institut National De La Recherche Agronomique	Compositions et procédés pour stimuler la croissance et le développement des plantes
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
JP2016510073A (ja)	2013-03-12	2016-04-04	バイエル・クロップサイエンス・アクチェンゲゼルシャフト	有用植物において細菌性有害生物を防除するためのジチイン−テトラカルボキシイミドの使用
CN105101776B (zh)	2013-03-28	2019-04-02	诺维信生物农业公司	用于增强微生物稳定性的组合物和方法
WO2015048627A1 (fr)	2013-09-30	2015-04-02	Bayer Cropscience Lp, A Delaware Limited Partnership	Souches de streptomyces microflavus et leurs procédés d'utilisation pour le traitement et la prévention de la maladie du dragon jaune
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
EP3097200A1 (fr) *	2014-01-24	2016-11-30	SynAffix B.V.	Procédé pour la fixation d'une fraction galnac comprenant un groupe (hétéro)aryle à une fraction glcnac, et produit ainsi obtenu
EP3097079B1 (fr)	2014-01-24	2021-05-12	SynAffix B.V.	Procédé de cycloaddition d'un composé hétéro(aryl) 1,3-dipôle avec un (hétéro)cycloalcyne
US10266502B2 (en)	2014-01-24	2019-04-23	Synaffix B.V.	Process for the cycloaddition of a halogenated 1,3-dipole compound with a (hetero)cycloalkyne
WO2015134256A1 (fr)	2014-02-28	2015-09-11	E. I. Du Pont De Nemours And Company	Bibliothèques combinatoires
EP3113611A1 (fr)	2014-03-05	2017-01-11	Novozymes A/S	Préparations contenant du xyloglucane polymère comme support d'agents bénéfiques sur le plan agricole
MX385401B (es)	2014-07-23	2025-03-18	Novonesis Plant Biosolutions As	Composiciones que contienen lipo-quitooligosacarido y microorganismo para potenciar el crecimiento de las plantas.
CN108024545A (zh)	2015-09-11	2018-05-11	诺维信生物农业公司	稳定的接种物组合物及其生产方法
UA129046C2 (uk)	2015-12-28	2025-01-01	Новонесіс Плант Біосолушнз А/С	Неводна композиція з інокулянтом
AU2016383059B2 (en)	2015-12-28	2022-10-27	Monsanto Technology Llc	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 (fr)	2016-05-31	2017-12-07	Novozymes Bioag A/S	Compositions d'inoculant liquides stables et materiaux de propagation de plantes enrobes comprenant celles-ci
US20200085065A1 (en)	2016-12-20	2020-03-19	Novozymes Bioag A/S	Stable inoculant compositions and methods for producing same
US20190320661A1 (en)	2017-01-03	2019-10-24	Monsanto Technology, Llc	Microbial compositions and methods
CA3048997A1 (fr)	2017-01-03	2018-07-12	Monsanto Technology Llc	Compositions microbiennes et procedes associes
EP3565886A1 (fr)	2017-01-04	2019-11-13	Novozymes BioAG A/S	Isolats de bacillus et utilisations de ces derniers
WO2018129018A1 (fr)	2017-01-05	2018-07-12	Novozymes Bioag A/S	Isolats de lysinibacillus et leurs utilisations
US11089776B2 (en)	2017-02-28	2021-08-17	Monsanto Technology Llc	Containerized liquid formulations
WO2018159393A1 (fr) *	2017-03-01	2018-09-07	花王株式会社	Agent favorisant la croissance de plantes légumineuses
AU2018237187B2 (en)	2017-03-24	2023-11-30	Novonesis Plant Biosolutions 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
BR112019024738A2 (pt)	2017-05-26	2020-06-16	Novozymes Bioag A/S	Uso de um ou mais óleos vegetais metilados, composição inoculante líquida, semente de planta revestida, kit, e, método
EP3629741A1 (fr)	2017-05-26	2020-04-08	Novozymes BioAG A/S	Compositions d'inoculums liquides stables comprenant du dodécane
WO2019006226A1 (fr)	2017-06-29	2019-01-03	Monsanto Technology Llc	Procédé de traitement de semences pour grands volumes de liquide
US12102084B2 (en)	2017-09-12	2024-10-01	Monsanto Technology Llc	Processes for the preparation of treated seeds
UA126979C2 (uk)	2018-01-08	2023-03-01	Новозімес Біоаґ А/С	Водна композиція, що містить солюбілізований ліпохітоолігосахарид
WO2019147660A1 (fr)	2018-01-23	2019-08-01	Novozymes Bioag A/S	Procédé d'amélioration de la germination de graines sous stress abiotique avec des oligosaccharides de chitine
US20210251236A1 (en)	2018-05-07	2021-08-19	Novozymes Bioag A/S	Microbacterium isolates and uses thereof
US12052942B2 (en)	2018-11-01	2024-08-06	Monsanto Technology Llc	Seed treater
WO2020263812A1 (fr)	2019-06-24	2020-12-30	Auburn University	Souche de bacillus et ses procédés d'utilisation pour la favorisation de la croissance des plantes
WO2020263734A1 (fr)	2019-06-24	2020-12-30	Novozymes Bioag A/S	Isolats d'erwinia et leurs utilisations
EP3818829A3 (fr)	2019-10-16	2021-07-21	Monsanto Technology LLC	Compositions nématicides granulaires
WO2021086695A1 (fr)	2019-10-29	2021-05-06	Novozymes Bioag A/S	Isolats de microbacterium et leurs utilisations
WO2021101937A1 (fr)	2019-11-20	2021-05-27	Novozymes Bioag A/S	Isolats de pseudomonas et leurs utilisations
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 (fr)	2020-12-08	2022-06-16	Monsanto Technology Llc	Bactéries modifiées associées à une plante et leurs procédés d'utilisation
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)

* Cited by examiner, † Cited by third party
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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Also Published As

Publication number	Publication date
CA2540074C (fr)	2012-05-15
BRPI0417892B1 (pt)	2015-01-06
MXPA06007465A (es)	2007-01-26
IN2006DE01668A (fr)	2007-08-10
EA009557B1 (ru)	2008-02-28
ZA200605258B (en)	2007-04-25
PT1701967E (pt)	2011-06-28
US7619076B2 (en)	2009-11-17
CN100549020C (zh)	2009-10-14
MA28296A1 (fr)	2006-11-01
ATE504593T1 (de)	2011-04-15
WO2005063784A1 (fr)	2005-07-14
KR101127785B1 (ko)	2012-04-12
FR2864538B1 (fr)	2006-03-03
US8198420B2 (en)	2012-06-12
JP5031376B2 (ja)	2012-09-19
AP2328A (en)	2011-11-28
FR2864538A1 (fr)	2005-07-01
US20110281729A1 (en)	2011-11-17
US8013132B2 (en)	2011-09-06
KR20060107831A (ko)	2006-10-16
AU2004309089A1 (en)	2005-07-14
BRPI0417892A (pt)	2007-04-27
AU2004309089B2 (en)	2011-03-10
DE602004032175D1 (de)	2011-05-19
IL175658A0 (en)	2006-09-05
CA2540074A1 (fr)	2005-07-14
US20070067921A1 (en)	2007-03-29
ES2364556T3 (es)	2011-09-06
MX258070B (es)	2008-06-20
AP2006003581A0 (en)	2006-04-30
JP2007517002A (ja)	2007-06-28
EA200601260A1 (ru)	2006-10-27
EP1701967A1 (fr)	2006-09-20
NZ546188A (en)	2010-03-26
US20100160167A1 (en)	2010-06-24
IL175658A (en)	2010-12-30
AR047174A1 (es)	2006-01-11
EP1701967B1 (fr)	2011-04-06
AR103791A2 (es)	2017-06-07
PL1701967T3 (pl)	2011-09-30
CN1882601A (zh)	2006-12-20

Publication	Publication Date	Title
OA13354A (en)	2007-04-13	Synthetic compounds useful as nodulation agents ofleguminous plants and preparation processes thereof.
EA018062B1 (ru)	2013-05-30	Пестицидная композиция, содержащая синтетическое соединение, полезное в качестве агента образования клубней бобовых растений, и фунгицидное соединение
NO141340B (no)	1979-11-12	Anilider for anvendelse som mikrobicider
US4799953A (en)	1989-01-24	Method for regulating plant growth using sulfur-containing organic acids
ZA200110461B (en)	2003-01-20	Use of glycuronic polysaccharides and oligosaccharides as phytosanitary products and/or fertilisers.
US4411684A (en)	1983-10-25	Auxin compositions of N-phenyl and N-chloro phenyl indolyl-3-alkylene amides and their use as auxin growth regulators
KR850001199B1 (ko)	1985-08-20	식물 성장 조절제의 제조방법
JPS6019901B2 (ja)	1985-05-18	新規な置換したコハク酸イミドおよび該イミドを含有する殺菌剤
JP2681669B2 (ja)	1997-11-26	新規なキトサン化合物、その製造方法および保湿剤としての用途
CN100334090C (zh)	2007-08-29	吡啶类鬼臼毒素化合物及其制备方法和在制备杀虫剂中的应用
US3184475A (en)	1965-05-18	Maleimides, maleamides and fumaramides
US5100456A (en)	1992-03-31	Herbicidal metabolites of phomopsis convoluvulus for the effective control of field bindweed
JP4382041B2 (ja)	2009-12-09	没食子酸誘導体およびその調製方法
AU658982B2 (en)	1995-05-04	Physiologically active substances of plant, process for the preparation thereof, and utilities thereof
US4846873A (en)	1989-07-11	1-carboalkoxyalkyl-3-alkoxy-4-(2'-carboxyphenyl)-azet-2-ones as plant growth regulators and selective herbicides
US3224936A (en)	1965-12-21	Pesticidal maleimides, maleamides and fumaramides
CN102665660A (zh)	2012-09-12	过氧化二苯甲酰衍生物、制备它们的方法、以及包含它们的美容或皮肤病组合物
CN120898855A (zh)	2025-11-07	一种植物源杀菌杀虫组合物及其制备方法和应用
Malik et al.	2014	Synthesis, Antimicrobial and Phytotoxic Activity of Amide Derivatives of L-(+)-2, 3-Diacetoxy-4-methoxy-4-oxo-butanoic acid.
PL233259B1 (pl)	2019-09-30	Indolilooctany 1-alkilochininy, sposób ich otrzymywania oraz zastosowanie jako środki bakteriostatyczne i bakteriobójcze
JPS63183598A (ja)	1988-07-28	抗生物質の製造法
FR2826007A1 (fr)	2002-12-20	Composes tetrahydrofuranes substitues presentant des proprietes antimicrobiennes, leurs procedes de preparation et les compositions les contenant