CN103130740A - Amino acid derivatives of seedvax and application for being used as bactericides thereof - Google Patents
Amino acid derivatives of seedvax and application for being used as bactericides thereof Download PDFInfo
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- CN103130740A CN103130740A CN2011103868648A CN201110386864A CN103130740A CN 103130740 A CN103130740 A CN 103130740A CN 2011103868648 A CN2011103868648 A CN 2011103868648A CN 201110386864 A CN201110386864 A CN 201110386864A CN 103130740 A CN103130740 A CN 103130740A
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- amino acid
- acid derivatives
- seedvax
- amicarthiazol
- bactericides
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- PQWGIVZSBVDSHW-UHFFFAOYSA-N Cc1c(NCC(O)=O)[s]c(C(Nc2ccccc2)=O)n1 Chemical compound Cc1c(NCC(O)=O)[s]c(C(Nc2ccccc2)=O)n1 PQWGIVZSBVDSHW-UHFFFAOYSA-N 0.000 description 1
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Abstract
The invention belongs to the technical field of chemical pesticide synthetic technology, and particularly relates to amino acid derivatives of a seedvax and the application of the amino acid derivatives of the seedvax for being used as bactericides. The amino acid derivatives of the seedvax is characterized in that the amino acid derivatives of the seedvax are of the structure shown in a general formula (I), the amino acid derivatives of the seedvax can be used as bactericides and can be used in the methods of seed dressing, mist spraying and daubing. The dosage form of the amino acid derivatives of the seedvax can be manufactured into missible oil, wettable powders or suspending agents. The amino acid derivatives can be conducted in dual directions inside a plant body, pesticides can be sprayed in the mode of moist through faces of leaves to prevent diseases of root portion of the plant and vascular bundles, and the amino acid derivatives of the seedvax has significant treatment and prevention effects of a rice sheath blight disease, a peanut rust disease, a corn smut, a cotton seedling stage disease and a wheat scab and the like.
Description
Technical field:
The invention belongs to the chemical pesticide synthesis technical field, specifically, relate to a kind of amino acid derivative of amicarthiazol and as the purposes of sterilant.
Background technology:
In the long-term practice that the mankind struggle with Plant diseases, the successful research and development of the systemic fungicides such as amicarthiazol make the disease control that the pathogenic bacteria that practise to occupy at inside plants causes obtain success greatly.But due to most of systemic fungicides enter in plant materials after all in apoplast conduction, i.e. unidirectional conduction from below to up is so be mainly used in carrying out soil treatment or the good protection effect of seed dressing competence exertion.Be difficult to the many vascular bundle diseases of control and root disease and spray by cauline leaf.But soil treatment can be brought serious environmental problem and the raising of drug cost.If can improve the transporting of systemic fungicide, can conduct at plant phloem, just can prevent and treat vascular bundle diseases of plant and root disease by spray method.If with easily compound and the effective combination of sterilant of conduction such as the amino acid in plant materials, and combining site do not shield the combining site of amino acid and carrier proteins, may make sterilant conduct to improve drug effect through phloem under amino acid whose guide effect.
Summary of the invention:
In order to overcome the deficiencies in the prior art, the object of the present invention is to provide a kind of amino acid derivative of amicarthiazol and as the purposes of sterilant.
The present invention realizes above-mentioned purpose by following technical solution.
The present invention by reacting with aldehyde, ketone compounds, generates schiff bases take amicarthiazol as starting raw material, under sodium borohydride reduction, obtains the amino acid derivative of amicarthiazol, and its general structure is as shown in (I):
In formula: R
1Be the straight chain of H, C1～C4 or the alkyl of C3～C4 side chain;
R
2Be the straight chain of H, C1～C4 or the alkyl of C3～C4 side chain.
The preparation method that the present invention has the compound of said structure general formula (I) is:
1, amicarthiazol is dissolved in ethanol or tetrahydrofuran (THF) or acetonitrile;
2, add oxoethanoic acid, perhaps glyoxylic ester, perhaps pyruvic acid, perhaps pyruvate, perhaps other meets ketone acid or its ester of following structural (II), reacts under 50～80 ℃ 3～5 hours, obtains the schiff base compounds of amicarthiazol;
In formula: R
1Be the straight chain of H, C1～C4 or the alkyl of C3～C4 side chain;
R
2Be the straight chain of H, C1～C4 or the alkyl of C3～C4 side chain;
3, then by sodium borohydride reduction, obtain the amino acid derivative of amicarthiazol, purify by column chromatography for separation, get the amino acid derivative product.
The concrete reaction formula of compound of the present invention is as shown in the formula shown in (III):
Amino acid derivative with compound amicarthiazol of said structure general formula (I) of the present invention can be used as sterilant, uses with seed dressing, spraying or smearing method; Its formulation is mixed with missible oil, wettable powder or suspension agent.
The use of spraying under 200～400mg/L concentration of the amino acid derivative of compound amicarthiazol of the present invention has unusual effect to the control of rice sheath blight disease, paddy rice bacterial leaf spot, bacterial stripe, Peanut Rust, smut of maize, disease in cotton seedling stage, bluish dogbane anthrax, wheat scab and rust, Colletotricum destructivum and sprout term disease.
Compared with prior art, the present invention is after deriving the amino acid functional group on the amicarthiazol molecular basis, due to the transport vehicle that has amino-acid compound in plant materials, identify by structure, the amino acid derivative that can deliver the amicarthiazol that contains the amino acid functional group can carry out Bidirectional Conduction in plant materials, the amino acid derivative of amicarthiazol has similar activity to amicarthiazol, therefore can prevent and treat plant root and vascular bundle diseases by the foliar spray dispenser.
Embodiment:
Embodiment 1:
Amicarthiazol glycine derivative synthetic, that is: 2-[(4 '-methyl-2 '-carbanilino)-thiazole-5 '-yl]-Padil synthetic.
The compound that the present embodiment 1 is synthetic, (I-I) is as follows for its structural formula:
Concrete synthesis step is: take the former medicine 7g of amicarthiazol (0.03mol) in round-bottomed flask, with the tetrahydrofuran (THF) dissolving, add the glyoxylic acid ethyl ester of 0.03mol, with temperature-stable at 50～70 ℃, back flow reaction 3～4 hours, thin-layer chromatography is followed the tracks of reaction process.Add the 0.05mol sodium borohydride after reacting completely, temperature is controlled at 25～30 ℃ of reactions 4～5 hours, thin-layer chromatography is followed the tracks of reaction process.After reacting completely, solvents tetrahydrofurane is steamed.The column chromatography separation and purification obtains target product 6.4g, productive rate 73%.
Target compound
1HNMR (400MHz, CD
3Cl) δ: 2.45 (s, 3H, CH
3), 3.98 (s, 2H, CH
2), 6.96～7.30 (m, 5H, C
6H
5).
Embodiment 2:
Amicarthiazol alanine derivatives synthetic, that is: 2-[(4 '-methyl-2 '-carbanilino)-thiazole-5 '-yl]-alanine synthetic.
The compound that the present embodiment 2 is synthetic, (I-II) is as follows for its structural formula:
Concrete steps are: take the former medicine 7g of amicarthiazol (0.03mol) in round-bottomed flask, with tetrahydrofuran (THF) dissolving, add the Pyruvic Acid Ethyl ester of 0.03mol, with temperature-stable at 50～70 ℃, back flow reaction 5 hours, thin-layer chromatography is followed the tracks of reaction process.Add the 0.05mol sodium borohydride after reacting completely, temperature is controlled at 25～30 ℃ of reactions 5 hours, thin-layer chromatography is followed the tracks of reaction process.After reacting completely, solvents tetrahydrofurane is steamed.The column chromatography separation and purification obtains target product 6.4g, productive rate 73%.
Target compound
1HNMR (400MHz, CD
3Cl) δ: 1.23 (d, 3H, CH
3-isoxazole), 2.47 (s, 3H, CH
3), 3.66 (t, H, CH), 6.86～7.30 (m, 5H, C
6H
5).
Embodiment 3:
Biological activity test:
Adopt mycelial growth rate to suppress method, measure the amicarthiazol amino acid derivative to the indoor bacteriostatic activity of rice sheath blight disease, and with the former medicine of amicarthiazol in contrast, calculate according to the following formula liquid to the inhibiting rate of mycelial growth, calculate medicament to the EC of Rhizoctonia solani Kuhn
50
The results are shown in table 1.Result can be found out from table, and amicarthiazol is still keeping same fungicidal activity after deriving the amino acid functional group, and along with the upper substituting group of amino acid functional group increases, activity exists downward trend.
Table 1: the fungicidal activity measurement result of amicarthiazol amino acid derivative and amicarthiazol
Embodiment 4:
Conductivity test 1: the conductivity test of amicarthiazol glycine derivative on tobacco.
Amicarthiazol glycine derivative 200mg/L concentration is coated with leaf to the blade of the tobacco plant middle part of 10～13 leaf phases processes, liquid phase chromatography detects different time and processes compounds content in blade and other blade, the results are shown in table 2.Result can be found out from table, and the amicarthiazol glycine derivative can both direction conduction up and down in the plant body.
Table 2: compounds content in Different sites of leaf after amicarthiazol glycine derivative processing tobacco plant
Embodiment 5:
Conductivity test 2: the conductivity test of amicarthiazol alanine ethyl ester derivative on tobacco.
Amicarthiazol alanine ethyl ester derivative 200mg/L concentration is coated with leaf to the tobacco plant middle part blades of 10～13 leaf phases processes, liquid phase chromatography detects different time and processes compounds content in blade and other blade and root, the results are shown in table 3.Result can be found out from table, amicarthiazol alanine ethyl ester derivative can be in the plant body both direction conduction up and down, and can conduct to root.
Table 3: different sites compounds content after amicarthiazol alanine ethyl ester derivative processing tobacco plant
Claims (3)
1. the amino acid derivative of an amicarthiazol, the structure shown in (I) that it is characterized in that having general formula:
In formula: R
1Be the straight chain of H, C1～C4 or the alkyl of C3～C4 side chain;
R
2Be the straight chain of H, C1～C4 or the alkyl of C3～C4 side chain.
2. the application of the amino acid derivative of a kind of amicarthiazol claimed in claim 1 is characterized in that using with seed dressing, spraying or smearing method as sterilant.
3. the application of the amino acid derivative of a kind of amicarthiazol according to claim 2 is characterized in that its formulation is mixed with missible oil, wettable powder or suspension agent.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011103868648A CN103130740A (en) | 2011-11-29 | 2011-11-29 | Amino acid derivatives of seedvax and application for being used as bactericides thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2011103868648A CN103130740A (en) | 2011-11-29 | 2011-11-29 | Amino acid derivatives of seedvax and application for being used as bactericides thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN103130740A true CN103130740A (en) | 2013-06-05 |
Family
ID=48491242
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2011103868648A Pending CN103130740A (en) | 2011-11-29 | 2011-11-29 | Amino acid derivatives of seedvax and application for being used as bactericides thereof |
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0206004A1 (en) * | 1985-06-13 | 1986-12-30 | Bayer Ag | E-isomers of N-alpha-(2-cyano-2-alkoxyiminoacetyl)-amino-acid derivatives and peptides |
| CN1033626A (en) * | 1987-06-25 | 1989-07-05 | 国际壳牌研究有限公司 | Thiazole derivative |
| CN1048386A (en) * | 1989-06-06 | 1991-01-09 | 鲁索-艾克勒夫公司 | Novel thiazole base alkoxy acrylic ester, they the preparation method, do the purposes of mycocide and prepare the intermediate of this compounds |
| CN1110506A (en) * | 1994-04-30 | 1995-10-25 | 河南省科学院化学研究所 | Cotton seed dressing agent with disease-prevention and insecticide function |
| JP2007210924A (en) * | 2006-02-08 | 2007-08-23 | Ishihara Sangyo Kaisha Ltd | Bactericidal composition containing carboxylic acid amide derivative |
| CN101265274A (en) * | 2007-02-16 | 2008-09-17 | 中国医学科学院药物研究所 | Pyrimidinthiazolamine derivatives, and preparation method, medicament composition and use thereof |
-
2011
- 2011-11-29 CN CN2011103868648A patent/CN103130740A/en active Pending
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0206004A1 (en) * | 1985-06-13 | 1986-12-30 | Bayer Ag | E-isomers of N-alpha-(2-cyano-2-alkoxyiminoacetyl)-amino-acid derivatives and peptides |
| CN1033626A (en) * | 1987-06-25 | 1989-07-05 | 国际壳牌研究有限公司 | Thiazole derivative |
| CN1048386A (en) * | 1989-06-06 | 1991-01-09 | 鲁索-艾克勒夫公司 | Novel thiazole base alkoxy acrylic ester, they the preparation method, do the purposes of mycocide and prepare the intermediate of this compounds |
| CN1110506A (en) * | 1994-04-30 | 1995-10-25 | 河南省科学院化学研究所 | Cotton seed dressing agent with disease-prevention and insecticide function |
| JP2007210924A (en) * | 2006-02-08 | 2007-08-23 | Ishihara Sangyo Kaisha Ltd | Bactericidal composition containing carboxylic acid amide derivative |
| CN101265274A (en) * | 2007-02-16 | 2008-09-17 | 中国医学科学院药物研究所 | Pyrimidinthiazolamine derivatives, and preparation method, medicament composition and use thereof |
Non-Patent Citations (2)
| Title |
|---|
| 李凯等: "杀菌剂在韧皮部的传导性研究进展", 《世界农药》 * |
| 黄青春: "羧酰胺类杀菌剂的活性及机理研究进展", 《世界农药》 * |
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Application publication date: 20130605 |