CA2260711C - Composes antibacteriens pour ralstonia solanacearum - Google Patents

Composes antibacteriens pour ralstonia solanacearum Download PDF

Info

Publication number: CA2260711C
Authority: CA; Canada
Prior art keywords: indolyl; butanoic acid; plant; antibacterial composition; salt
Prior art date: 1998-02-05
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 - Fee Related

Application number

CA 2260711

Other languages

English (en)

Other versions

CA2260711A1 (fr

Inventor

Kazuhiko Matsuda

Hideyoshi Toyoda

Satoshi Harada

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Kagome Co Ltd

Original Assignee

Kagome Co Ltd

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.)

1998-02-05

Filing date

1999-02-04

Publication date

2005-03-15

1998-02-05 Priority claimed from JP10041317A external-priority patent/JPH11228310A/ja

1999-02-04 Application filed by Kagome Co Ltd filed Critical Kagome Co Ltd

1999-08-05 Publication of CA2260711A1 publication Critical patent/CA2260711A1/fr

2005-03-15 Application granted granted Critical

2005-03-15 Publication of CA2260711C publication Critical patent/CA2260711C/fr

2019-02-04 Anticipated expiration legal-status Critical

Status Expired - Fee Related legal-status Critical Current

Links

230000000844 anti-bacterial effect Effects 0.000 title claims abstract description 20
241000589771 Ralstonia solanacearum Species 0.000 title claims abstract description 17
150000001875 compounds Chemical class 0.000 title claims abstract description 15
IKTJMKYSKNYTJM-QMMMGPOBSA-N (3s)-3-(1h-indol-3-yl)butanoic acid Chemical compound C1=CC=C2C([C@H](CC(O)=O)C)=CNC2=C1 IKTJMKYSKNYTJM-QMMMGPOBSA-N 0.000 claims abstract description 22
150000003839 salts Chemical class 0.000 claims abstract description 17
230000001580 bacterial effect Effects 0.000 claims abstract description 14
230000012010 growth Effects 0.000 claims abstract description 14
239000000203 mixture Substances 0.000 claims description 23
239000007788 liquid Substances 0.000 claims description 16
IKTJMKYSKNYTJM-UHFFFAOYSA-N 3-(1h-indol-3-yl)butanoic acid Chemical compound C1=CC=C2C(C(CC(O)=O)C)=CNC2=C1 IKTJMKYSKNYTJM-UHFFFAOYSA-N 0.000 claims description 14
238000000034 method Methods 0.000 claims description 12
241000196324 Embryophyta Species 0.000 claims description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
150000002148 esters Chemical class 0.000 claims description 8
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 claims description 6
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 6
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
230000002401 inhibitory effect Effects 0.000 claims description 6
239000004367 Lipase Substances 0.000 claims description 4
108090001060 Lipase Proteins 0.000 claims description 4
102000004882 Lipase Human genes 0.000 claims description 4
240000003768 Solanum lycopersicum Species 0.000 claims description 4
-1 alkali metal salt Chemical class 0.000 claims description 4
150000003863 ammonium salts Chemical class 0.000 claims description 4
239000007795 chemical reaction product Substances 0.000 claims description 4
235000019421 lipase Nutrition 0.000 claims description 4
238000010992 reflux Methods 0.000 claims description 4
235000008534 Capsicum annuum var annuum Nutrition 0.000 claims description 3
240000008384 Capsicum annuum var. annuum Species 0.000 claims description 3
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 3
240000009088 Fragaria x ananassa Species 0.000 claims description 3
235000007688 Lycopersicon esculentum Nutrition 0.000 claims description 3
244000088415 Raphanus sativus Species 0.000 claims description 3
235000006140 Raphanus sativus var sativus Nutrition 0.000 claims description 3
244000061458 Solanum melongena Species 0.000 claims description 3
235000002597 Solanum melongena Nutrition 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 3
229910052802 copper Inorganic materials 0.000 claims description 3
239000010949 copper Substances 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
238000010438 heat treatment Methods 0.000 claims description 3
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 3
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 3
GXHFUVWIGNLZSC-UHFFFAOYSA-N meldrum's acid Chemical compound CC1(C)OC(=O)CC(=O)O1 GXHFUVWIGNLZSC-UHFFFAOYSA-N 0.000 claims description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
235000021012 strawberries Nutrition 0.000 claims description 3
244000061176 Nicotiana tabacum Species 0.000 claims description 2
235000002637 Nicotiana tabacum Nutrition 0.000 claims description 2
238000007259 addition reaction Methods 0.000 claims description 2
239000007859 condensation product Substances 0.000 claims description 2
238000006114 decarboxylation reaction Methods 0.000 claims description 2
230000007062 hydrolysis Effects 0.000 claims description 2
238000006460 hydrolysis reaction Methods 0.000 claims description 2
159000000000 sodium salts Chemical class 0.000 claims description 2
239000007787 solid Substances 0.000 claims description 2
239000004615 ingredient Substances 0.000 claims 5
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
238000002474 experimental method Methods 0.000 description 9
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
230000000694 effects Effects 0.000 description 6
239000002904 solvent Substances 0.000 description 6
IKTJMKYSKNYTJM-MRVPVSSYSA-N (3r)-3-(1h-indol-3-yl)butanoic acid Chemical compound C1=CC=C2C([C@@H](CC(O)=O)C)=CNC2=C1 IKTJMKYSKNYTJM-MRVPVSSYSA-N 0.000 description 5
244000309560 Ralstonia solanacearum race 1 Species 0.000 description 5
125000004494 ethyl ester group Chemical group 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 4
230000002378 acidificating effect Effects 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
239000012295 chemical reaction liquid Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000000499 gel Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
230000003287 optical effect Effects 0.000 description 3
239000000047 product Substances 0.000 description 3
239000000243 solution Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
239000000872 buffer Substances 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
239000000645 desinfectant Substances 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
238000010898 silica gel chromatography Methods 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
241000894006 Bacteria Species 0.000 description 1
208000035143 Bacterial infection Diseases 0.000 description 1
108010023063 Bacto-peptone Proteins 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
108090000371 Esterases Proteins 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
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 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
208000022362 bacterial infectious disease Diseases 0.000 description 1
239000012267 brine Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
230000002925 chemical effect Effects 0.000 description 1
239000013078 crystal Substances 0.000 description 1
238000004042 decolorization Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000010828 elution Methods 0.000 description 1
238000000605 extraction Methods 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000008103 glucose Substances 0.000 description 1
230000009545 invasion Effects 0.000 description 1
210000004185 liver Anatomy 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
239000012528 membrane Substances 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000011148 porous material Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
238000009877 rendering Methods 0.000 description 1
230000002786 root growth Effects 0.000 description 1
230000009528 severe injury Effects 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
239000002689 soil Substances 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1

Landscapes

Agricultural Chemicals And Associated Chemicals (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA 2260711 1998-02-05 1999-02-04 Composes antibacteriens pour ralstonia solanacearum Expired - Fee Related CA2260711C (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
JP10041317A JPH11228310A (ja)	1998-02-05	1998-02-05	青枯れ病菌拮抗剤
JP10-41317		1998-02-05
US09/229,207 US6015830A (en)	1998-02-05	1999-01-13	Antibacterial compounds for Ralstonia solanacearum
US09/229,207		1999-01-13

Publications (2)

Publication Number	Publication Date
CA2260711A1 CA2260711A1 (fr)	1999-08-05
CA2260711C true CA2260711C (fr)	2005-03-15

Family

ID=29585884

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA 2260711 Expired - Fee Related CA2260711C (fr)	1998-02-05	1999-02-04	Composes antibacteriens pour ralstonia solanacearum

Country Status (1)

Country	Link
CA (1)	CA2260711C (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP3560328B2 (ja) *	2000-06-27	2004-09-02	カゴメ株式会社	藻類又は苔の発生抑制剤
CN100412058C (zh) *	2005-05-12	2008-08-20	苏州大学	一种双吲哚烷基化合物的合成方法

1999
- 1999-02-04 CA CA 2260711 patent/CA2260711C/fr not_active Expired - Fee Related

Also Published As

Publication number	Publication date
CA2260711A1 (fr)	1999-08-05

Legal Events

Date	Code	Title	Description
2000-03-21	EEER	Examination request
2016-03-17	MKLA	Lapsed	Effective date: 20160204

Publication	Publication Date	Title
DE68919184T2 (de)	1995-04-13	Verfahren zur Herstellung von optisch aktiven 3-Phenylglycidsäureestern.
US6015830A (en)	2000-01-18	Antibacterial compounds for Ralstonia solanacearum
EP0032659A1 (fr)	1981-07-29	Dérivés optiquement actifs de phénylpropane, leur préparation et utilisation pour la préparation de fongicides
DE3886445T2 (de)	1994-05-19	Optisch-aktive Verbindungen und Verfahren zu deren Herstellung.
CA2260711C (fr)	2005-03-15	Composes antibacteriens pour ralstonia solanacearum
US4385186A (en)	1983-05-24	Optically active 4-hydroxy-3-methyl-2-(2-propynyl)-2-cyclopentenone
JPH0160239B2 (fr)	1989-12-21
DE19955283A1 (de)	2001-05-23	Verfahren zur enantioselektiven Gewinnung von Aminosäuren und Aminosäurederivaten unter Verwendung von Racemisierungskatalysatoren
US20230150895A1 (en)	2023-05-18	Soil conditioner and use thereof
JPS5878594A (ja)	1983-05-12	抗生物質ｂ−４１ｄ、ｅ及びｇの製造法
JP2746372B2 (ja)	1998-05-06	Ｆ−０３６８物質
EP0395106B1 (fr)	1994-07-06	Déméthylallosamidine et procédé pour sa production
AU617344B2 (en)	1991-11-28	A process for the enzymatic preparation of optically active phosphorus-containing functional acetic acid derivatives
US5493063A (en)	1996-02-20	Process for optical resolution of 1,2-diol derivatives
EP1688501B1 (fr)	2009-08-26	Procédé de préparation de manool et de manool cétone
EP0576834A2 (fr)	1994-01-05	Procédé de production de dérivés d'un 1,2-diol optiquement active
MXPA99001306A (en)	2000-07-01	Antibacterial compounds for ralstonia solanacea
US5846791A (en)	1998-12-08	N-(R)-(2-hydroxy-2-pyridine-3-yl-ethyl)-2-(4-nitro-phenyl)-acetamide
JP3273965B2 (ja)	2002-04-15	生理活性物質ｍｊ２８６−ａ物質、その製造法及び除草剤の薬害軽減剤
JPH0656774A (ja)	1994-03-01	光学活性（＋）−４，４，４−トリフルオロ −３−（インド−ル−３−）酪酸およびその製造方法
JP3202824B2 (ja)	2001-08-27	光学活性ヒドロキシニトリルの製法及びこの製法において使用する新規な合成中間体
US3835170A (en)	1974-09-10	Hypotensive agent, oudenone, its salts and processes for production and preparation thereof
JP2002003309A (ja)	2002-01-09	藻類又は苔の発生抑制剤
HU208311B (en)	1993-09-28	Resolving process for producing enantiomers of 2-/4-(5-trifluoromethyl-2-pyridyloxy)-phenoxy/-propanoic acid
JPH01299268A (ja)	1989-12-04	抗真菌性発酵産生物及びその誘導体及びその組成物