CN112244031A - Application of thiothiadiazole-containing nitrothiazole compound in prevention and treatment of agricultural plant diseases - Google Patents
Application of thiothiadiazole-containing nitrothiazole compound in prevention and treatment of agricultural plant diseases Download PDFInfo
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Abstract
The invention relates to the field of medicinal chemistry, and discloses application of 5- ((5-nitrothiazole-2-yl) thio) -1,3, 4-thiadiazole compounds H-1-H-8 in resisting plant pathogenic bacteria. Biological activity tests show that the compound of the invention has potential inhibitory activity on 8 agricultural diseases such as rhizoctonia solani, sclerotinia sclerotiorum, fusarium graminearum, botrytis cinerea, fusarium oxysporum, rice blast, citrus canker and potato phytophthora parasitica, and part of the compound has higher inhibitory activity. The compound is simple to prepare, the raw materials are cheap and easy to obtain, and the compound is expected to be developed into a novel bacteriostatic agent.
Description
Technical Field
The invention belongs to the field of medicinal chemistry, discloses a new application of 5- ((5-nitrothiazol-2-yl) thio) -1,3, 4-thiadiazole compounds, and particularly relates to an application of 5- ((5-nitrothiazol-2-yl) thio) -1,3, 4-thiadiazole compounds H-1-H-8 in preventing and treating rhizoctonia solani, sclerotinia sclerotiorum, fusarium graminearum, botrytis cinerea, fusarium oxysporum, pyricularia oryzae, citrus canker and potato phytophthora parasitica.
Background
Phytopathogens are one of the most harmful phytopathogenic microorganisms, which can cause serious plant diseases and reduced yield of crops. At present, people mainly control the plant pathogenic bacteria infection through chemical pesticides, but with the use of the chemical pesticides, the problems of drug resistance, environmental pollution, residue toxicity and the like continuously appear, and new challenges are provided for the prevention and control of plant fungi and bacterial diseases. Therefore, the search for novel anti-phytopathogen drugs is an urgent problem to be solved at present.
The 5- ((5-nitrothiazol-2-yl) thio) -1,3, 4-thiadiazole compound is a c-Jun N-terminal kinase inhibitor and has the functions of improving cardiac function and ischemia-reperfusion injury. In recent studies, the compound is found to have good antibacterial activity to human beings, and particularly has obvious inhibition effect on escherichia coli, and further studies show that the compound can inhibit the growth of pathogenic bacteria by selectively releasing transmembrane DpH potential, and is a novel antibacterial compound with a structure different from that of the traditional antibiotics.
Therefore, we have conducted activity tests on this compound and its analogues against phytopathogens. The results show that the compounds all have certain activity against plant pathogenic bacteria, wherein the compound H-1 has good activity against plant fungi and bacteria, has broad spectrum, has activity obviously superior to that of positive control azoxystrobin and bismerthiazol, and is expected to be developed into a novel plant pathogenic bacteria resistant medicament.
Disclosure of Invention
The invention provides the following technical method: a medicine for resisting rhizoctonia solani, sclerotinia sclerotiorum, fusarium graminearum, botrytis cinerea, fusarium oxysporum, pyricularia oryzae, citrus canker and potato phytophthora parasitica contains a therapeutically effective amount of any 5- ((5-nitrothiazol-2-yl) thio) -1,3, 4-thiadiazole compound from H-1 to H-8, and the structure of the compound is shown in chemical formula 1.
The preparation method of the 5- ((5-nitrothiazole-2-yl) thio) -1,3, 4-thiadiazole compounds H-1-H-8 is shown in chemical formulas 2 and 3:
the synthesis method of the 5- ((5-nitrothiazole-2-yl) thio) -1,3, 4-thiadiazole compound is shown in the embodiment, a pure product is obtained by separation of conventional methods such as silica gel column chromatography for many times, and the structures of the compounds H-1-H-8 are determined by spectrum techniques such as mass spectrum and nuclear magnetic resonance, and the structural formula is shown in chemical formula 1. The activity screening result shows that the compound of the invention has a certain degree of inhibiting effect on rhizoctonia solani, sclerotinia sclerotiorum, fusarium graminearum, botrytis cinerea, fusarium oxysporum, rice blast, citrus canker and potato phytophthora parasitica.
Detailed Description
The foregoing and other aspects of the present invention will become more apparent from the following detailed description, given by way of example only, for purposes of illustrating the invention. This is not to be construed as limiting the invention. The experimental procedures described in the following examples are conventional unless otherwise specified.
EXAMPLE 1 Synthesis of Compound H-1
The synthesis method of the compound H-1 is carried out according to the following reaction formula:
synthesis of Compound H-1 5-amino-1, 3, 4-thiadiazole-2-thiol (1mmol) was dissolved in methanol (25mL), sodium methoxide (1.5mmol) was added thereto, and after stirring for 10min, 2-bromo-5-nitrothiazole (1mmol) was added thereto, and reacted for 6-7 hours. After the reaction is finished, adding a proper amount of 1mmol HCl solution into the solvent, stirring for 10min, performing suction filtration, and adding petroleum ether and petroleum ether: the mixed solution of ethyl acetate (10:1) was washed 3 times. And collecting filter residues and drying to obtain the target compound H-1.
Yield: 66.3 percent; a yellow solid;1HNMR(400MHz,DMSO-d6)δ:8.74(s,1H),7.94(s,2H).13C NMR(100MHz,DMSO-d6)δ:173.51,171.25,148.68,144.45,140.54.MS-ESIm/z:C5H3N5O2S3:261.9[M+H]+。
EXAMPLE 2 Synthesis of Compound H-2
The synthesis method of the compound H-2 is carried out according to the following reaction formula:
synthesis of compound H-2, under ice bath condition, compound H-1(1mmol) is added into DMF (15mL) and stirred to dissolve, then NaH (3mmol) is added into the solution and stirred for 30min, then 1-bromo-3-methyl-2-butene (1mmol) is slowly dropped and reacted for 4 hours at normal temperature. After the reaction is finished, adding excessive saturated ammonium chloride to quench the reaction, stirring for 5min, extracting with dichloromethane, combining organic phases, and purifying by column chromatography to obtain the target compound H-2.
Yield: 67.5 percent; a yellow oily liquid;1H NMR(400MHz,CDCl3)δ:8.35(s,1H),5.42–5.28(m,1H),3.92(d,J＝7.8Hz,2H),1.77(s,3H),1.76(s,3H).13C NMR(100MHz,CDCl3)δ:174.79,143.51,140.28,116.58,32.36,25.89,18.23.MS-ESI m/z:C10H11N5O2S3:330.0[M+H]+
EXAMPLE 3 Synthesis of Compound H-3
The experimental procedure was the same as in example 2, except that 1-bromo-3-methyl-2-butene was replaced with 1-bromo-n-hexane. Yield: 64.3 percent; a yellow oily liquid;1H NMR(400MHz,CDCl3)δ:8.34(s,1H),3.27(t,J＝7.4Hz,2H),1.85–1.76(m,2H),1.50–1.31(m,4H),0.92(t,J＝7.1Hz,3H).13C NMR(100MHz,CDCl3)δ:175.13,143.55,34.07,30.97,28.60,22.25,14.01.MS-ESIm/z:C10H13N5O2S3:332.0[M+H]+。
EXAMPLE 4 Synthesis of Compound H-4
The experimental procedure was the same as in example 2, except that 4-fluorobenzyl bromide was used instead of 1-bromo-3-methyl-2-butene. Yield: 74.0%; a yellow-green solid;1H NMR(400MHz,CDCl3)δ:8.37(s,1H),7.38(dd,J＝8.6,5.3Hz,2H),7.10–6.98(m,2H),4.50(s,2H).13C NMR(100MHz,CDCl3)δ:173.12,162.64(d,J＝246Hz),147.81(d,J＝3Hz),143.26,130.98(d,J＝8Hz),116.01(d,J＝22Hz),37.11.MS-ESIm/z:C12H8FN5O2S3:370.0[M+H]+。
EXAMPLE 5 Synthesis of Compound H-5
The experimental procedure is as in example 2, replacing 1-bromo-3-methyl-2-butene only with 1-n-bromo-butane. Yield: 67.7 percent; a yellow oily liquid;1H NMR(400MHz,CDCl3)δ:8.34(s,1H),3.28(t,J＝7.3Hz,2H),1.83–1.74(m,2H),1.54–1.44(m,2H),0.97(t,J＝7.4Hz,3H).13C NMR(100MHz,CDCl3)δ:175.12,143.55,33.79,30.91,22.04,13.64.MS-ESI m/z:C9H11N5O2S3:318.0[M+H]+。
EXAMPLE 6 Synthesis of Compound H-6
The synthesis method of the compound H-6 is carried out according to the following reaction formula:
synthesis of Compound H-6 Compound H-1(1mmol) was dissolved in dichloromethane (25mL) with stirring, triethylamine (2mmol) was added to the solution with stirring for 10min, then isovaleryl chloride (1.2mmol) was slowly added dropwise and reacted at room temperature for 4 hours. And after the reaction is finished, distilling under reduced pressure to remove the solvent, extracting by using dichloromethane and brine, combining organic phases, and purifying by using column chromatography to obtain the target compound H-6.
Yield: 66.7 percent; a yellow solid;1H NMR(400MHz,CDCl3)δ:12.97(s,1H),8.45(s,1H),2.69(d,J＝7.1Hz,2H),2.42–2.20(m,1H),1.06(d,J＝6.6Hz,6H).13C NMR(100MHz,CDCl3)δ:171.73,167.54,163.73,151.41,143.21,45.25,29.85,26.54,22.55.MS-ESIm/z:C10H11N5O3S3:346.0[M+H]+。
example 7 Synthesis of Compound H-7
The experimental procedure was the same as in example 6, except thatP-fluorobenzoyl chloride was substituted for isovaleryl chloride. Yield: 66.4 percent; a yellow solid;1H NMR(400MHz,DMSO-d6)δ:13.52(s,1H),8.78(s,1H),8.20(dd,J＝9.1,5.4Hz,2H),7.46–7.38(m,2H).13C NMR(100MHz,DMSO-d6)δ:168.51,165.07(d,J＝251Hz),164.64,163.40,150.80,149.07,144.12,131.55(d,J＝10Hz),127.54,115.87(d,J＝22Hz).MS-ESIm/z:C12H6FN5O3S3:384.0[M+H]+。
example 8 Synthesis of Compound H-8
Synthesis of Compound H-8 the experimental procedure was the same as in example 1, except that 5- (4-fluorophenyl) -1,3, 4-thiadiazole-2-thiol was used instead of 5-amino-1, 3, 4-thiadiazole-2-thiol. Yield: 67.4 percent; a yellow-green solid;1H NMR(400MHz,CDCl3)δ:8.47(s,1H),7.98(dd,J＝8.9,5.2Hz,2H),7.25–7.20(m,2H).13C NMR(100MHz,CDCl3)δ:170.98,165.87,165.10(d,J＝253Hz),156.18,149.92,142.86,130.37(d,J＝9Hz),125.50(d,J＝4Hz),116.96(d,J＝22Hz).MS-ESIm/z:C11H5FN4O2S3:341.0[M+H]+。
example 9 test method and results for antifungal Activity of 5- ((5-Nitrothiazol-2-yl) thio) -1,3, 4-thiadiazole Compounds H-1 to H-8
1) The reagent 5- ((5-nitrothiazole-2-yl) thio) -1,3, 4-thiadiazole compounds H-1-H-8.
2) Test strains: rhizoctonia solani, sclerotinia sclerotiorum, fusarium graminearum, botrytis cinerea, fusarium wilt and rice blast.
3) And (3) testing antibacterial activity:
the test method comprises the following steps: the antibacterial activity was measured using potato dextrose agar medium (PDA medium). The preparation method comprises the following steps: firstly, cleaning and peeling potatoes, weighing 200g of potatoes, cutting the potatoes into small pieces, adding water, boiling the potatoes thoroughly (boiling for 20-30 minutes, the potato pieces can be punctured by a glass rod), filtering the potatoes by eight layers of gauze, heating the potatoes, adding 15g of agar, continuously heating, stirring the mixture evenly, adding glucose after the agar is dissolved, stirring the mixture evenly, slightly cooling the mixture, then supplementing the water to 1000 ml, subpackaging the mixture in conical bottles, plugging and binding the conical bottles, and sterilizing the mixture for 2 hours at 115 ℃ for later use. Respectively dissolving the compounds H-01-H-22 in DMSO, adding the dissolved compounds into a culture medium, uniformly mixing to ensure that the concentrations of the compounds in the culture medium are respectively 100 mu g/mL, taking DMSO with equal concentration as a blank control, and taking the azoxystrobin which is a commercial drug as a positive control. And (3) pouring the plates, cooling, inoculating bacteria respectively, culturing in an incubator at 23 ℃, and determining the bacteriostasis rate of each compound by taking blank control hypha to overgrow the culture dish as a limit. All experiments were performed in triplicate or in triplicate. The calculation of the bacteriostasis rate is carried out according to the following calculation formula:
the bacteriostasis rate is (blank control hypha growth diameter-hypha growth diameter)/(blank control hypha growth diameter-fungus cake diameter) x 100%
The results of the activity test of 5- ((5-nitrothiazol-2-yl) thio) -1,3, 4-thiadiazole compounds H-1 to H-8 on 6 plant pathogenic fungi are shown in Table 1.
TABLE 1100 ppm inhibition ratio (%) (5-nitrothiazol-2-yl) thio) -1,3, 4-thiadiazole compounds H-1 to H-8 against pathogenic fungi)
As shown in Table 1, the compounds have certain inhibition effect on 6 plant fungal diseases, wherein the compound H-1 has good antibacterial activity and broad-spectrum property, and the inhibition rate at the concentration of 100ppm is 100%, so that the compound H-1 is further subjected to activity test, and the test results are shown in Table 2.
TABLE 2 results of Activity test of H-1 against 6 plant pathogenic fungi
As can be seen from Table 2, the inhibition rate of the compound H-1 on 6 plant fungi is still higher than 50% at a concentration of 25ppm, which is obviously superior to that of the positive control azoxystrobin.
Example 10 test method and results for the anti-plant-bacterial Activity of 5- ((5-Nitrothiazol-2-yl) thio) -1,3, 4-thiadiazole Compounds H-1 to H-8
1) Reagent to be tested: 5- ((5-nitrothiazol-2-yl) thio) -1,3, 4-thiadiazole compounds H-1-H-8.
2) Test strains: citrus canker pathogen and potato phytophthora parasitica.
3) And (3) testing antibacterial activity:
the test method comprises the following steps: the orange canker and potato black shank pathogens were streaked on MH solid medium (beef powder: 2g, soluble starch 1.5g, acid hydrolyzed casein: 17.5g, agar: 15g, distilled water: 1L; sterilized at 121 ℃ for 20min), and cultured at 25 ℃ until single colonies grew out. Single colonies of orange canker and potato phytophthora parasitica on an MHA solid culture medium are picked to an MH liquid culture medium (beef powder: 2g, soluble starch 1.5g, acid hydrolyzed casein: 17.5g, distilled water: 1L, sterilization at 121 ℃ for 20min), and shake-cultured to a logarithmic phase in a constant temperature shaking table at 25 ℃ and 180 rpm. Bacteria in logarithmic growth phase were diluted to about 10 with MH liquid medium6CFU/mL is ready for use. The compound and the commercial contrast agent are respectively dissolved in DMSO, added into MH liquid culture medium, and mixed evenly to prepare MH liquid culture medium containing medicament with the concentration of 200 mug/mL. Taking 50 μ L of medicated culture medium and the same volume of the medicated culture medium containing 106CFU/mL bacterial culture was added to the wells of a 96-well plate at a final dosing concentration of 100. mu.g/mL. 100 μ L of the same concentration of the bacterial suspension containing the same amount of DMSO was used as a control. Culturing 96-well plate in 25 deg.C incubator for 24 hr, and measuring OD value (OD) of bacterial liquid in the well on enzyme labeling instrument600). In addition, OD values of 100. mu.L MH liquid medium and the drug at a concentration of 100. mu.g/mL were measured, and the OD values due to the medium and the drug themselves were corrected. The calculation formula for correcting the OD value and the inhibition rate is as follows:
correcting OD value-bacteria-containing culture medium OD value-sterile culture OD value;
inhibition rate (OD value of control culture medium liquid after correction-OD value of drug-containing culture medium after correction)/OD value of control culture medium liquid after correction × 100%
The results of the activity tests of 5- ((5-nitrothiazol-2-yl) thio) -1,3, 4-thiadiazole and its analogs H-1 to H-8 against 2 plant pathogenic bacteria are shown in Table 3.
Inhibition ratio (%) of 5- ((5-nitrothiazol-2-yl) thio) -1,3, 4-thiadiazole compounds H-1 to H-8 against pathogenic bacteria at a concentration of 3100 ppm
As can be seen from Table 3, the compounds H-2 to H-8 showed lower inhibitory activity against Leptosphaeria citricola, and the inhibitory activity against potato phytophthora parasitica was superior to that against Leptosphaeria citricola. The compound H-1 shows excellent inhibitory activity to citrus canker pathogen and potato phytophthora parasitica at 100ppm, and the inhibition rate is 100%. Therefore, we performed further activity tests on compound H-1, and the results are shown in Table 4.
TABLE 4 Activity test results of H-1 against 2 plant pathogenic bacteria
As can be seen from Table 4, the compound H-1 still has an inhibition rate of more than 80% on the citrus canker pathogen and the potato phytophthora parasitica at a concentration of 6.25ppm, and is obviously superior to the positive control drug bismerthiazol.
In conclusion, the 5- ((5-nitrothiazole-2-yl) thio) -1,3, 4-thiadiazole compound shows certain inhibitory activity on plant pathogenic fungi and bacteria, wherein the inhibitory activity of H-1 is obviously superior to that of positive control drugs azoxystrobin and bismerthiazol, and has the characteristic of broad spectrum. The compound has simple synthesis method and cheap and easily obtained raw materials, and is expected to be developed into a novel antibacterial agent for plant fungi and bacteria.
Claims (10)
1. The invention relates to an application of 5- ((5-nitrothiazole-2-yl) thio) -1,3, 4-thiadiazole compounds H-1-H-8 in preparation of a medicament for preventing and treating or resisting phytopathogens.
2. The 5- ((5-nitrothiazol-2-yl) thio) -1,3, 4-thiadiazole compound according to claim 1, which has the following molecular structural features:
3. the use of any one of the 5- ((5-nitrothiazol-2-yl) thio) -1,3, 4-thiadiazole compounds H-1 to H-8 according to claim 1 in the preparation of a medicament for the prevention or treatment of rhizoctonia solani.
4. The use of any one of the 5- ((5-nitrothiazol-2-yl) thio) -1,3, 4-thiadiazole compounds H-1-H-8 according to claim 1 in the preparation of a medicament for the control or resistance of sclerotinia sclerotiorum.
5. The use of any one of the 5- ((5-nitrothiazol-2-yl) thio) -1,3, 4-thiadiazole compounds H-1 to H-8 according to claim 1 in the preparation of a medicament for the prevention or treatment of triticum aestivum.
6. The use of any one of the 5- ((5-nitrothiazol-2-yl) thio) -1,3, 4-thiadiazole compounds H-1 to H-8 according to claim 1 in the preparation of a medicament for the prevention or treatment of botrytis cinerea.
7. The use of any one of the 5- ((5-nitrothiazol-2-yl) thio) -1,3, 4-thiadiazole compounds H-1 to H-8 according to claim 1 in the preparation of a medicament for the prevention or treatment of cotton wilt.
8. The use of any one of 5- ((5-nitrothiazol-2-yl) thio) -1,3, 4-thiadiazole compounds H-1 to H-8 according to claim 1 in the preparation of a medicament for controlling or resisting Pyricularia oryzae.
9. The use of any one of the 5- ((5-nitrothiazol-2-yl) thio) -1,3, 4-thiadiazole compounds H-1-H-8 according to claim 1 in the preparation of a medicament for the control or resistance of citrus canker bacteria.
10. The use of any one of the 5- ((5-nitrothiazol-2-yl) thio) -1,3, 4-thiadiazole compounds H-1-H-8 according to claim 1 in the preparation of a medicament for controlling or resisting leptosphaeria maculans.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112979637A (en) * | 2021-03-16 | 2021-06-18 | 扬州市普林斯医药科技有限公司 | Thiazole compound with antibacterial property and application thereof |
| CN113694060A (en) * | 2021-09-09 | 2021-11-26 | 山东省农业科学院家禽研究所（山东省无特定病原鸡研究中心） | Application of nitrothiazole derivative, hydrochloride and sulfate thereof in preparation of medicines for treating intestinal infection of livestock and poultry |
| CN113994971A (en) * | 2021-11-25 | 2022-02-01 | 兰州大学 | Use of kinase inhibitors for controlling phytopathogenic bacteria |
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| US20110319455A1 (en) * | 2010-04-19 | 2011-12-29 | Bruce Steven Klein | Antifungal Treatment |
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| US4097669A (en) * | 1975-07-26 | 1978-06-27 | Bayer Aktiengesellschaft | 2-Substituted-5-trifluoromethyl-1,3,4-thiadiazoles |
| US4209522A (en) * | 1978-06-28 | 1980-06-24 | The Dow Chemical Company | Antimicrobial bis(5-nitro-2-thiazolyl)thioisothiazoles and thiadiazoles |
| US20110319455A1 (en) * | 2010-04-19 | 2011-12-29 | Bruce Steven Klein | Antifungal Treatment |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN112979637A (en) * | 2021-03-16 | 2021-06-18 | 扬州市普林斯医药科技有限公司 | Thiazole compound with antibacterial property and application thereof |
| CN112979637B (en) * | 2021-03-16 | 2022-05-31 | 扬州市普林斯医药科技有限公司 | Thiazole compound with antibacterial property and application thereof |
| CN113694060A (en) * | 2021-09-09 | 2021-11-26 | 山东省农业科学院家禽研究所（山东省无特定病原鸡研究中心） | Application of nitrothiazole derivative, hydrochloride and sulfate thereof in preparation of medicines for treating intestinal infection of livestock and poultry |
| CN113994971A (en) * | 2021-11-25 | 2022-02-01 | 兰州大学 | Use of kinase inhibitors for controlling phytopathogenic bacteria |
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Application publication date: 20210122 |