CA2260711C - Antibacterial compounds for ralstonia solanacearum - Google Patents
Antibacterial compounds for ralstonia solanacearum Download PDFInfo
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- CA2260711C CA2260711C CA 2260711 CA2260711A CA2260711C CA 2260711 C CA2260711 C CA 2260711C CA 2260711 CA2260711 CA 2260711 CA 2260711 A CA2260711 A CA 2260711A CA 2260711 C CA2260711 C CA 2260711C
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- butanoic acid
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Abstract
Antibacterial compounds for Ralstonia solanacearum having substantially (S)-3-(3-indolyl) butanoic acid of a specified structure or its salt as active component can selectively inhibit the growth of Ralstonia solanacearum and suppress bacterial wilt dependably even if used at relatively lower concentration.
Description
Background of the Invention This invention relates to antibacterial compounds for Ralstonia solanacearum. Bacterial wilt which affects tomatoes, egg plants, green peppers, tobacco plants, radishes, strawberries and the like is a.kind of bacterial disease caused by Ralstonia solanacearum. Ralstonia solanacearum is known for its very high spreading velocity, and its secondary invasion is very strong. Thus, the bacterial wilt caused thereby can be a source of a severe damage particularly for green-house cultivation and repeated cultivation. This invention relates to antibacterial compounds capable of dependably suppressing such bacterial wilt even if used at a low concentration.
Conventional methods of suppressing bacterial wilt included disinfection by the solar heat, root growth restriction by means of sheets and grafting on resistant cultivar as rootstocks. With these conventional methods, however, manifestation of effects is extremely insufficient.
Use of a disinfectant has also been attempted but the use of a disinfectant has bad effects not only on the plants and the soil but also on the workers, besides suppressing bacterial wilt. In view of the above, Japanese Patent Publication Tokkai 7-228502 disclosed the use of synthesized 3-(3-indoly:l) butanoic acid and its salts as antibacterial compounds capable of suppressing Ralstonia solanacearum. These compounds have the desirable characteristic of being capable of selectively inhibiting the growth of Ralstonia solanacearum which is the cause of bacterial wilt and hence suppressing bacterial wilt without having any ill effects on other bodies. Prior art synthesized 3-(3-indolyl)butanoic acid and its salts have the disadvantage, however, in that they must be used at a relatively high concentration in order to selectively inhibit the growth of Ralstonia solanacearum.
Summary of the Invention It is therefore an object of this invention to provide an antibacterial compound capable of selectively suppressing the growth of Ralstonia solanacearum even if used at a relatively low concentration.
This invention is based on the present inventors' discovery that synthesized 3-(3-indolyl)butanoic acid is a racemic body containing both optical isomers (S)-3-(3-indolyl)-butanoic acid (which is the S body of 3-(3-indolyl)butanoic acid) and (R)-3-(3-indolyl)butanoic acid (which is the R body of ~-(3-indolyl)butanoic acid) and that it is the former of these~two that has a significant chemical effect in selectively inhibiting the growth of Ralstonia solanacearum and is hence capable of dependably suppressing bacterial wilt, even if used at a relatively low concentration, without having any ill effects on other bodies.
Detailed Description of the Invention 'This invention relates to substantially pure (S)-3-(3-indolyl)butanoic acid of the formula:
COOH
Formula (1) N
H
_2_ or a salt thereof.
Synthesized 3-(3-indolyl)butanoic acid is a racemic mixture which contains as optical isomers both aforementioned (S)-3-(3-indolyl)butanoic acid shown by Formula (1) and (R)-3--(3-indolyl)butanoic acid of the formula:
COON
Formula (2 ) .
N
H
As will be shown below more in detail, (S)-3-(3-indolyl)butanoic acid of the Formula (1) above can be obtained through the following three steps: (1) first step wherein a condensation product of meldrum's acid and acetoaldehyde is caused to undergo an addition reaction with indole to obtain a reaction product; (2) second step wherein the reaction product obtained in the first step is dissolved in a mixed liquid of pyridine and an alcohol, copper is added thereto and a decarboxylation reaction is caused by heating under reflux to obtain esters of a racemic mixture of 3-(3-indolyl)butanoic acid; and (3) third step wherein the esters obtained in the second step are subjected to an enzymic process by using lipase which is capable of selectively dissociating by hydrolysis only esters of (S)-3-(3-indolyl)butanoic acid contained in the aforementioned esters obtained in the second step to thereby obtain (S)-3-(3-indolyl)butanoic acid.
Examples of the salts of (S)-3-(3-indolyl)butanoic acid of Formula (1) include those of an alkali metal such as potassium and sodium, those of an alkali earth metal such as calcium and magnesium and ammonium salt.
As will be described below in more detail, (S)-3-(3-indolyl)butanoic acid shown by Formula (1) and its salts are more effective in selectively preventing the growth of Ralstonia solanacearum than (R)-3-(3-indolyl)butanoic acid or its salts, and also more effective than the racemic body of 3-(3-indolyl)-butanoic acid which is a mixture of these two, as well as its salts, and hence can dependently suppress bacterial wilt even at a low concentration without rendering any ill effects to other bodies.
Preferred for use as an antibacterial compound for Ralstonia solanacearum are (S)-3-(3-indolyl)butanoic acid, t:he sodium salt thereof, and the ammonium salt thereof.
The compound of the Formula (1) or its salt may be used as it is or in the form of a composition (i. e., mixtures or formulation) containing a suitable carrier or diluent in addition to an antibacterial effective amount of the compound or salt. The carrier or diluent may be liquid or solid and :is usually suitable for use in the agricultural or horticultural field.
It is more common to use the compound or salt in the form of the composition. It is generally well known how to formulate the composition for use as an antibacterial composition for the application to plants. Therefore, detailed descriptions of materials and procedures for producing the composition are not necessary here. Generally, such a composition contains the compound or salt as an active ingred-Tent in an amount of from about 0.01 up to 90$ by weight.
The compound of the Formula (1) or its salt may be applied for inhibiting the growth of Ralstonia solanacearum to plants or habitat thereof. The manner of application may generally be the same as that of the known racemic mixture of 3-(3-indolyl) butanoic acid or its salt, except that the amount (or concentration) of the active ingredient may be reduced.
The invention will be explained next by way of the results of experiments carried out.
Experiment Part 1:
Indole 3g and meldrum's acid 4.43g were dissolved in 30m1 of acetontrile, and 3m1 each of acetaldehyde refined immediately before by distillation was added both at the beginning time of the reaction and 2 hours later to cause a reaction at 30°C for 6 hours with stirring. After the reaction liquid was condensed at a reduced pressure, it was dissolved in a mixed solvent of pyridine 30m1 and ethanol 3m1, and copper particles 150mg were added for a reaction by heating under reflux for 6 hours. After the reaction liquid was filtered and the filtered liquid was made acidic (according to its pH) by adding 2N hydrochloric acid, ether -4a-was used for extraction. The extracted liquid was washed with water and after it was dried with anhydrous magnesium sulfate, the solvent was distilled away under a reduced pressure. The residue was refined by silica gel column chromatography (gel .
Wakogel C-200 (trade-mark of product by Wako Pure Chemical Industries, Ltd.); solvent . hexane/ethyl acetate = 5/1) to obtain 2.25g of ethyl ester of racemic body of 3-(3-indolyl) butanoic acid. A 1/1 mixture 20m1 of ethanol and 10% aqueous solution of potassium hydroxide was added to this ethyl ester l0 of racemic body of 3-(3-indolyl) butanoic acid 2.258, and it was dried and hardened by means of an evaporator after 6 hours of reflux. Water was added to this hardened dry substance, .
and it was washed with ether. After active charcoal was added for decolorization with heat, it was filtered to remove the active charcoal. Crystal 1.85g of racemic body of 3-(3-indolyl) butanoic acid was obtained by adding 2N hydrochloric .acid to the decolored liquid to make the solution acidic.
Experiment Part 2:
Ethyl ester 53.6mg of racemic body of 3-(3-indolyl) 2o butanoic acid, produced during the course of Experiment Part 1 was dissolved in O.iM acetic acid buffer (pH=5) containing t-butanol by l0%, and Lipase AK (trade mark of product by Amano Pharmaceutical Co., Ltd.) The reaction liquid was filtered with Celite* and, after the filtered liquid was made acidic (according to its pH) by adding 1N hydrochloric acid, it was extracted by using ethyl acetate. After the extracted liquid was dried with anhydrous sodium sulfate, the solvent was distilled away under a reduced pressure. The residue was analyzed through a silica gel column (gel . Wakogel). First, ethyl ester 13.4mg of (R)-3-(3-indolyl) butanoic acid not decomposed by Lipase AK was eluted out by using a mixture of dichloromethane/ethyl acetate = 9/1 as solvent. Next, (S)-3-(3-indolyl) butanoic acid l3.lmg was obtained by elution by using a mixture of dichloromethane/ethyl acetate = 1/1. The *Trade-mark -5-optical purity of (S)-3-~(3-indolyl) butanoic acid by a high performance liquid chromatography (HPLC) method was 99%.
Experiment Part 3:
The ethyl ester l3mg of (R)-3-(3-indolyl) butanoic:
acid obtained in Experiment Part 2 above was dissolved in O.1M phosphoric acid buffer (pH = 7.3) containing t-butanol by 10%. Porcine liver esterase (trade name of product by Sigma-Aldrich Co'.) 62mg was added to this solution for a reaction at 30°C. for 24 hours with stirring. The reaction liquid was filtered and after 1N hydrochloric acid was added to the filtered liquid to make it acidic (according to its pH), it was extracted by using ethyl acetate. The extracted liquid was washed with water and after it was dried by using anhydrous sodium sulfate, the solvent was distilled away under a reduced pressure. The residue was refined by silica gel column chromatography (gel . Wakogel C-200; solvent .
dichloromethane/ethyl acetate = 1/1) to obtain 7mg of (R)-3-(3-indolyl) butanoic acid. Its optical purity by the HPLC
'method was 99%.
experiment pa-rt 4:
By the minimum inhibitory concentration (MIC) method which will be described in detail below, antibacterial activities against Ralstonia solanacearum race 1 of the racemic body, the S body and the R body of 3-(3-indolyl) butanoic acid obtained in Experiment Parts 1, 2 and 3 described above were measured. The results are shown in Table 1 below. -According to this MIC method, the racemic body, the 3o S body and the R body of 3-(3-indolyl) butanoic acid obtained in Experiment Parts 1, 2 and 3 were each dissolved in 4%
methyl alcohol and these solutions were each mixed with an equal amount of a double-strength PCG liquid medium (bacto-peptone lOg + casamino acid lg + glucose lOg per liter) such that the concentrations (in ~g/ml) of the racemic body, the: S
body and the R body would be as given in Table 1. The lic~;~id medium thus prepared was filtered through a membrane of pore size 0.22~m to reduce the bacteria count to provide a test medium. Separately, Ralstonia solanacearum race 1 bacteria were preliminarily cultivated by using a PCG liquid medium and after they were collected, a bacterial suspension of 5 x 105 cell/ml was obtained in physiological brine. This bacterial suspension 601 was inoculated to 3m1 of the aforementioned test medium and stirred for cultivation at 30°C
for 24 hours. The growth of Ralstonia solanacearum race 1 bacteria was measured by using as indicator the turbidity of this culture liquid at 600nm. Since the turbidity of the culture liquid would be the same as that of an uninoculated culture liquid if the growth of Ralstonia solanacearum race 1 bacteria were completely inhibited by the racemic, S or R
body, the concentration of the racemic, S or R body at such a time was defined as the MIC.
Concentration 0 0.5 1.0 2.5 5 10 25 (~g/ml) Growth Racemic body + + + - - -S body + + - _ _ - .-R body + + + + + -In viable 1:
+: Growth observed -: Growth inhibited Table 1 shows that the MIC of 3-(3-indolyl) butanoic acid against Ralstonia solanacearum race 1 is about 10~g/ml in the case of R body and about 2.5~g/ml in the case of racemic body but that it is about only l.O~g/ml in the case of S body. This means that the use of (S)-3-(3-indolyl) butanoic acid or its salt as antibacterial compound is far more effective in inhibiting the growth of Ralstonia solanacearum and hence in _7_ dependably and selectively suppressing bacterial wilt even if used at a relatively lower concentration without causing any ill effects on other bodies.
_g_
Conventional methods of suppressing bacterial wilt included disinfection by the solar heat, root growth restriction by means of sheets and grafting on resistant cultivar as rootstocks. With these conventional methods, however, manifestation of effects is extremely insufficient.
Use of a disinfectant has also been attempted but the use of a disinfectant has bad effects not only on the plants and the soil but also on the workers, besides suppressing bacterial wilt. In view of the above, Japanese Patent Publication Tokkai 7-228502 disclosed the use of synthesized 3-(3-indoly:l) butanoic acid and its salts as antibacterial compounds capable of suppressing Ralstonia solanacearum. These compounds have the desirable characteristic of being capable of selectively inhibiting the growth of Ralstonia solanacearum which is the cause of bacterial wilt and hence suppressing bacterial wilt without having any ill effects on other bodies. Prior art synthesized 3-(3-indolyl)butanoic acid and its salts have the disadvantage, however, in that they must be used at a relatively high concentration in order to selectively inhibit the growth of Ralstonia solanacearum.
Summary of the Invention It is therefore an object of this invention to provide an antibacterial compound capable of selectively suppressing the growth of Ralstonia solanacearum even if used at a relatively low concentration.
This invention is based on the present inventors' discovery that synthesized 3-(3-indolyl)butanoic acid is a racemic body containing both optical isomers (S)-3-(3-indolyl)-butanoic acid (which is the S body of 3-(3-indolyl)butanoic acid) and (R)-3-(3-indolyl)butanoic acid (which is the R body of ~-(3-indolyl)butanoic acid) and that it is the former of these~two that has a significant chemical effect in selectively inhibiting the growth of Ralstonia solanacearum and is hence capable of dependably suppressing bacterial wilt, even if used at a relatively low concentration, without having any ill effects on other bodies.
Detailed Description of the Invention 'This invention relates to substantially pure (S)-3-(3-indolyl)butanoic acid of the formula:
COOH
Formula (1) N
H
_2_ or a salt thereof.
Synthesized 3-(3-indolyl)butanoic acid is a racemic mixture which contains as optical isomers both aforementioned (S)-3-(3-indolyl)butanoic acid shown by Formula (1) and (R)-3--(3-indolyl)butanoic acid of the formula:
COON
Formula (2 ) .
N
H
As will be shown below more in detail, (S)-3-(3-indolyl)butanoic acid of the Formula (1) above can be obtained through the following three steps: (1) first step wherein a condensation product of meldrum's acid and acetoaldehyde is caused to undergo an addition reaction with indole to obtain a reaction product; (2) second step wherein the reaction product obtained in the first step is dissolved in a mixed liquid of pyridine and an alcohol, copper is added thereto and a decarboxylation reaction is caused by heating under reflux to obtain esters of a racemic mixture of 3-(3-indolyl)butanoic acid; and (3) third step wherein the esters obtained in the second step are subjected to an enzymic process by using lipase which is capable of selectively dissociating by hydrolysis only esters of (S)-3-(3-indolyl)butanoic acid contained in the aforementioned esters obtained in the second step to thereby obtain (S)-3-(3-indolyl)butanoic acid.
Examples of the salts of (S)-3-(3-indolyl)butanoic acid of Formula (1) include those of an alkali metal such as potassium and sodium, those of an alkali earth metal such as calcium and magnesium and ammonium salt.
As will be described below in more detail, (S)-3-(3-indolyl)butanoic acid shown by Formula (1) and its salts are more effective in selectively preventing the growth of Ralstonia solanacearum than (R)-3-(3-indolyl)butanoic acid or its salts, and also more effective than the racemic body of 3-(3-indolyl)-butanoic acid which is a mixture of these two, as well as its salts, and hence can dependently suppress bacterial wilt even at a low concentration without rendering any ill effects to other bodies.
Preferred for use as an antibacterial compound for Ralstonia solanacearum are (S)-3-(3-indolyl)butanoic acid, t:he sodium salt thereof, and the ammonium salt thereof.
The compound of the Formula (1) or its salt may be used as it is or in the form of a composition (i. e., mixtures or formulation) containing a suitable carrier or diluent in addition to an antibacterial effective amount of the compound or salt. The carrier or diluent may be liquid or solid and :is usually suitable for use in the agricultural or horticultural field.
It is more common to use the compound or salt in the form of the composition. It is generally well known how to formulate the composition for use as an antibacterial composition for the application to plants. Therefore, detailed descriptions of materials and procedures for producing the composition are not necessary here. Generally, such a composition contains the compound or salt as an active ingred-Tent in an amount of from about 0.01 up to 90$ by weight.
The compound of the Formula (1) or its salt may be applied for inhibiting the growth of Ralstonia solanacearum to plants or habitat thereof. The manner of application may generally be the same as that of the known racemic mixture of 3-(3-indolyl) butanoic acid or its salt, except that the amount (or concentration) of the active ingredient may be reduced.
The invention will be explained next by way of the results of experiments carried out.
Experiment Part 1:
Indole 3g and meldrum's acid 4.43g were dissolved in 30m1 of acetontrile, and 3m1 each of acetaldehyde refined immediately before by distillation was added both at the beginning time of the reaction and 2 hours later to cause a reaction at 30°C for 6 hours with stirring. After the reaction liquid was condensed at a reduced pressure, it was dissolved in a mixed solvent of pyridine 30m1 and ethanol 3m1, and copper particles 150mg were added for a reaction by heating under reflux for 6 hours. After the reaction liquid was filtered and the filtered liquid was made acidic (according to its pH) by adding 2N hydrochloric acid, ether -4a-was used for extraction. The extracted liquid was washed with water and after it was dried with anhydrous magnesium sulfate, the solvent was distilled away under a reduced pressure. The residue was refined by silica gel column chromatography (gel .
Wakogel C-200 (trade-mark of product by Wako Pure Chemical Industries, Ltd.); solvent . hexane/ethyl acetate = 5/1) to obtain 2.25g of ethyl ester of racemic body of 3-(3-indolyl) butanoic acid. A 1/1 mixture 20m1 of ethanol and 10% aqueous solution of potassium hydroxide was added to this ethyl ester l0 of racemic body of 3-(3-indolyl) butanoic acid 2.258, and it was dried and hardened by means of an evaporator after 6 hours of reflux. Water was added to this hardened dry substance, .
and it was washed with ether. After active charcoal was added for decolorization with heat, it was filtered to remove the active charcoal. Crystal 1.85g of racemic body of 3-(3-indolyl) butanoic acid was obtained by adding 2N hydrochloric .acid to the decolored liquid to make the solution acidic.
Experiment Part 2:
Ethyl ester 53.6mg of racemic body of 3-(3-indolyl) 2o butanoic acid, produced during the course of Experiment Part 1 was dissolved in O.iM acetic acid buffer (pH=5) containing t-butanol by l0%, and Lipase AK (trade mark of product by Amano Pharmaceutical Co., Ltd.) The reaction liquid was filtered with Celite* and, after the filtered liquid was made acidic (according to its pH) by adding 1N hydrochloric acid, it was extracted by using ethyl acetate. After the extracted liquid was dried with anhydrous sodium sulfate, the solvent was distilled away under a reduced pressure. The residue was analyzed through a silica gel column (gel . Wakogel). First, ethyl ester 13.4mg of (R)-3-(3-indolyl) butanoic acid not decomposed by Lipase AK was eluted out by using a mixture of dichloromethane/ethyl acetate = 9/1 as solvent. Next, (S)-3-(3-indolyl) butanoic acid l3.lmg was obtained by elution by using a mixture of dichloromethane/ethyl acetate = 1/1. The *Trade-mark -5-optical purity of (S)-3-~(3-indolyl) butanoic acid by a high performance liquid chromatography (HPLC) method was 99%.
Experiment Part 3:
The ethyl ester l3mg of (R)-3-(3-indolyl) butanoic:
acid obtained in Experiment Part 2 above was dissolved in O.1M phosphoric acid buffer (pH = 7.3) containing t-butanol by 10%. Porcine liver esterase (trade name of product by Sigma-Aldrich Co'.) 62mg was added to this solution for a reaction at 30°C. for 24 hours with stirring. The reaction liquid was filtered and after 1N hydrochloric acid was added to the filtered liquid to make it acidic (according to its pH), it was extracted by using ethyl acetate. The extracted liquid was washed with water and after it was dried by using anhydrous sodium sulfate, the solvent was distilled away under a reduced pressure. The residue was refined by silica gel column chromatography (gel . Wakogel C-200; solvent .
dichloromethane/ethyl acetate = 1/1) to obtain 7mg of (R)-3-(3-indolyl) butanoic acid. Its optical purity by the HPLC
'method was 99%.
experiment pa-rt 4:
By the minimum inhibitory concentration (MIC) method which will be described in detail below, antibacterial activities against Ralstonia solanacearum race 1 of the racemic body, the S body and the R body of 3-(3-indolyl) butanoic acid obtained in Experiment Parts 1, 2 and 3 described above were measured. The results are shown in Table 1 below. -According to this MIC method, the racemic body, the 3o S body and the R body of 3-(3-indolyl) butanoic acid obtained in Experiment Parts 1, 2 and 3 were each dissolved in 4%
methyl alcohol and these solutions were each mixed with an equal amount of a double-strength PCG liquid medium (bacto-peptone lOg + casamino acid lg + glucose lOg per liter) such that the concentrations (in ~g/ml) of the racemic body, the: S
body and the R body would be as given in Table 1. The lic~;~id medium thus prepared was filtered through a membrane of pore size 0.22~m to reduce the bacteria count to provide a test medium. Separately, Ralstonia solanacearum race 1 bacteria were preliminarily cultivated by using a PCG liquid medium and after they were collected, a bacterial suspension of 5 x 105 cell/ml was obtained in physiological brine. This bacterial suspension 601 was inoculated to 3m1 of the aforementioned test medium and stirred for cultivation at 30°C
for 24 hours. The growth of Ralstonia solanacearum race 1 bacteria was measured by using as indicator the turbidity of this culture liquid at 600nm. Since the turbidity of the culture liquid would be the same as that of an uninoculated culture liquid if the growth of Ralstonia solanacearum race 1 bacteria were completely inhibited by the racemic, S or R
body, the concentration of the racemic, S or R body at such a time was defined as the MIC.
Concentration 0 0.5 1.0 2.5 5 10 25 (~g/ml) Growth Racemic body + + + - - -S body + + - _ _ - .-R body + + + + + -In viable 1:
+: Growth observed -: Growth inhibited Table 1 shows that the MIC of 3-(3-indolyl) butanoic acid against Ralstonia solanacearum race 1 is about 10~g/ml in the case of R body and about 2.5~g/ml in the case of racemic body but that it is about only l.O~g/ml in the case of S body. This means that the use of (S)-3-(3-indolyl) butanoic acid or its salt as antibacterial compound is far more effective in inhibiting the growth of Ralstonia solanacearum and hence in _7_ dependably and selectively suppressing bacterial wilt even if used at a relatively lower concentration without causing any ill effects on other bodies.
_g_
Claims (12)
1. An antibacterial composition for a plant bacterial wilt caused by Ralstonia solanacearum, which comprises:
(i) (S)-3-(3-indolyl)butanoic acid of the following Formula:
or a salt thereof, and, (ii) a suitable carrier or diluent, wherein the ingredient (i) is contained in an amount of 0.01 to 90% by weight based on the antibacterial composition.
(i) (S)-3-(3-indolyl)butanoic acid of the following Formula:
or a salt thereof, and, (ii) a suitable carrier or diluent, wherein the ingredient (i) is contained in an amount of 0.01 to 90% by weight based on the antibacterial composition.
2. The antibacterial composition according to claim 1, wherein the ingredient (i) is an alkali metal salt of (S)-3-(3-indolyl)butanoic acid.
3. The antibacterial composition according to claim 1, wherein the ingredient (i) is sodium salt of (S)-3-(3-indolyl)butanoic acid.
4. The antibacterial composition according to claim 1, wherein the ingredient (i) is ammonium salt of (S)-3-(3-indolyl)butanoic acid.
5. The antibacterial composition according to claim 1,, wherein the ingredient (i) is (S)-3-(3-indolyl)butanoic acid.
6. The antibacterial composition according to any one of claims 1 to 5 in a liquid or solid form adapted for application to a plant in an agricultural or horticultural field.
7. The antibacterial composition according to claim 6, wherein the plant is selected from the group consisting of tomatoes, egg plants, green peppers, tobacco plants, radishes and strawberries.
8. A process for producing (S)-3-(3-indolyl)butanoic acid of the Formula 1 of claim 1, which comprises:
a first step wherein a condensation product of meldrum's acid and acetoaldehyde is caused to undergo an addition reaction with indole to obtain a reaction product, a second step wherein the reaction product of the first step is dissolved in a mixed liquid of pyridine and an alcohol, copper is added thereto and a decarboxylation reaction is caused by heating under reflux to obtain esters of racemic body of 3-(3-indolyl)butanoic acid, and a third step wherein the esters obtained in the second step are subjected to an enzymic process by using lipase which is capable of selectively dissociating by hydrolysis only esters of (S)-3-(3-indolyl)butanoic acid contained in the esters obtained in the second step to thereby obtain (S)-3-(3-indolyl)butanoic acid.
a first step wherein a condensation product of meldrum's acid and acetoaldehyde is caused to undergo an addition reaction with indole to obtain a reaction product, a second step wherein the reaction product of the first step is dissolved in a mixed liquid of pyridine and an alcohol, copper is added thereto and a decarboxylation reaction is caused by heating under reflux to obtain esters of racemic body of 3-(3-indolyl)butanoic acid, and a third step wherein the esters obtained in the second step are subjected to an enzymic process by using lipase which is capable of selectively dissociating by hydrolysis only esters of (S)-3-(3-indolyl)butanoic acid contained in the esters obtained in the second step to thereby obtain (S)-3-(3-indolyl)butanoic acid.
9. A method for inhibiting the growth of Ralstonia solanacearum on a plant, which comprises:
applying an antibacterial effective amount of the compound (S)-3-(3-indolyl)butanoic acid of the following Formula:
applying an antibacterial effective amount of the compound (S)-3-(3-indolyl)butanoic acid of the following Formula:
10 or a salt thereof, to the plant or habitat thereof.
10. The method according to claim 9, wherein the plant is selected from the group consisting of tomatoes, egg plants, green peppers, tomato plants, radishes and strawberries.
10. The method according to claim 9, wherein the plant is selected from the group consisting of tomatoes, egg plants, green peppers, tomato plants, radishes and strawberries.
11. The method according to claim 10, wherein the plant is grown in a green house.
12. The method according to any one of claims 9 to 11, wherein an alkali metal salt or ammonium salt of (S)-3-(3-indolyl)butanoic acid is employed.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10-41317 | 1998-02-05 | ||
| JP10041317A JPH11228310A (en) | 1998-02-05 | 1998-02-05 | Antagonistic agent against bacterial wilt-causing microorganism |
| 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 (en) | 1999-08-05 |
| CA2260711C true CA2260711C (en) | 2005-03-15 |
Family
ID=29585884
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA 2260711 Expired - Fee Related CA2260711C (en) | 1998-02-05 | 1999-02-04 | Antibacterial compounds for ralstonia solanacearum |
Country Status (1)
| Country | Link |
|---|---|
| CA (1) | CA2260711C (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3560328B2 (en) * | 2000-06-27 | 2004-09-02 | カゴメ株式会社 | Algae or moss generation inhibitor |
| CN100412058C (en) * | 2005-05-12 | 2008-08-20 | 苏州大学 | Process for synthesizing bis-indolyl alkyl compounds |
-
1999
- 1999-02-04 CA CA 2260711 patent/CA2260711C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2260711A1 (en) | 1999-08-05 |
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