CN102850341A - Thiadiazole compound, preparation method and applications thereof - Google Patents
Thiadiazole compound, preparation method and applications thereof Download PDFInfo
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Abstract
The present invention relates to a thiadiazole compound and a preparation method thereof. The thiadiazole compound has a structure represented by a formula (I), wherein R is C1-C4 alkyl or substituted phenyl, the substituted group of the substituted phenyl is independently selected from hydrogen, C1-C4 alkyl, and a halogen. The thiadiazole compound of the present invention has characteristics of simple preparation and excellent bactericidal activity, and can be used as a bactericidal agent for prevention and control of cucumber tan disease, cucumber bacterial angular leaf spot disease, cucumber gummy stem blight, cucumber downy mildew, and cucumber sclerotium disease. The present invention further relates to a bactericidal agent containing the compound.
Description
Technical field
The present invention relates to a kind of thiadiazole compound, 5-(5-replacement-4-phenyl-4H-1 specifically, 2,4-triazolyl)-the 4-methyl isophthalic acid, 2,3-thiadiazoles derivative and preparation and application thereof.
Background technology
Heterogeneous ring compound has been the main flow of novel pesticide development, and in heterogeneous ring compound, again take nitrogen heterocyclic ring as main.Thiadiazole compound is a more rapidly class of development in recent years, and many commercial sterilant belong to such.For example, the sterilant lythidathion with interior absorption of the former industry of Japanese stone company exploitation has the stronger ability of killing for the various insects that traditional sterilant produced resistance; The triticonazole of SUMITOMO CHEMICAL chemical company exploitation in 1974 is a kind of systemic fungicide, and the formation that infect hypha on the spore is adhered in inhibition prevents rice blast.1,2,3 thiadiazole compounds are more rapidly classes of development in recent years, many commercial desinsections, sterilization, weedicide, and plant induced resistance agent belongs to such.For example, the sterilant tiadinil (thIadInal) with interior absorption of Japanese agricultural chemicals company exploitation is mainly used in the control of rice blast, and other diseases such as brown spot, bacterial leaf-blight, banded sclerotial blight and sesame leaf rot etc. are also had preferably prevention effect; The N-(5-methyl-1,3-thiazole-2-yl)-4-methyl-1,2,3-thiadiazole of Nankai University's exploitation has good sterilization and induction of resistance effect.And the induced resistance of plant activiator BIon(BTH of Novartis Co.,Ltd's exploitation).
Yet, there is not yet relevant 5-(5-replacement-4-phenyl-4H-1,2,4-triazolyl)-the 4-methyl isophthalic acid, the bibliographical information of the synthetic and bioactivity research of 2,3-thiadiazoles derivative.
Summary of the invention
The object of the invention provides a kind of 5-(5-replacement-4-phenyl-4H-1 with fungicidal activity, 2,4-triazolyl)-the 4-methyl isophthalic acid, 2,3-thiadiazoles derivative and preparation method thereof and application.
The object of the present invention is achieved like this:
Thiadiazole compound shown in the formula (I):
In the formula (I): R is C1-C4 alkyl or substituted-phenyl, and the substituting group of described substituted-phenyl is selected from hydrogen, C1-C4 alkyl, halogen.
Formula of the present invention (I) compound can make by the following method: formula (II) compound and formula (III) compound are mixed with organic solvent, in the presence of alkaline matter, 0 ~ 25 ℃ of (preferred 25 ℃) stirring reaction, TLC follows the tracks of reaction (take the sherwood oil of volume ratio 1:1 ~ 5 and ethyl acetate mixture as developping agent, following the tracks of raw material point disappears for reacting completely), after reacting completely, reaction solution is placed frozen water, separate out solid, filter, filtrate is carried out silica gel column chromatography, and (sherwood oil take volume ratio as 5:1 and ethyl acetate mixture are eluent, collection contains the elutriant of target components, drying) or with recrystallization solvent carry out recrystallization, the thiadiazole compound shown in the acquisition formula (I);
Recrystallization solvent is one or more in sherwood oil, ethyl acetate, normal hexane or the ethanol, the mixing solutions of preferred sherwood oil and ethyl acetate;
Organic solvent is one or more in DMF, tetrahydrofuran (THF), Isosorbide-5-Nitrae-dioxane or the acetone, is preferably DMF (DMF);
Alkaline matter is one or more in salt of wormwood, sodium bicarbonate, sodium hydroxide, potassium hydroxide or the sodium hydride, is preferably salt of wormwood;
The ratio of the amount of substance of formula (II) compound, formula (III) compound and alkaline matter is 1:1.0 ~ 1.5:1.0 ~ 1.5, is preferably 1:1.0:1.2; The organic solvent volumetric usage is counted 2-10ml/mmol with formula (II) compound amount of substance, preferred 4ml/mmol.
In formula (I), the formula (III): R's is described as defined above, and R is halogen in the formula (III).
Formula (II) compound can make as follows:
The present invention also provides the application of the thiadiazole compound shown in the formula (I) in control Cucumber Target Leaf Spot, cucumber bacterial angular leaf spot, the climing rot of cucumber, cucumber downy mildew, cucumber timberrot.
The present invention also provides the sterilant that contains the thiadiazole compound shown in the formula (I), and it also comprises acceptable auxiliary agent at least a agricultural chemicals.
Compared with prior art, beneficial effect of the present invention is mainly reflected in: the invention provides its preparation method and the application of a kind of thiadiazole compound and intermediate, this compound is the new compound with fungicidal activity, for the research and development of novel pesticide provide the foundation.
Embodiment
The present invention is described further below in conjunction with specific embodiment, but protection scope of the present invention is not limited in this:
Embodiment 1
Synthesizing of thiadiazoles intermediate formula (II) compound: add 10mmol compound 4-methyl isophthalic acid in the 100 mL there-necked flasks, 2,3-thiadiazoles hydrazides and 40mL dehydrated alcohol splash into 10mmol phenyl thiocyanic ester, and a large amount of white solids appear in backflow 3h.Cold filtration is directly used in next step reaction after the oven dry.Add 10 mmol above-claimed cpds and 15 mL 2N NaOH solution in the 50 mL round-bottomed flasks, 4 h that reflux, 4N hydrochloric acid is neutralized to neutrality, produces a large amount of white solids, filters, and drying is with the white needle-like crystals of second alcohol and water recrystallization.
Embodiment 2
Target compound is the synthetic of formula (I) compound: add the K that 2 mmol compound I I, 2 mmol replace benzyl chloride, 8mL DMF and 2.4mmol in the 25 mL round-bottomed flasks
2CO
3, stirring at room, TLC detection reaction progress.React complete after, in the reaction solution impouring 30mL frozen water, separate out solid, filter, precipitation, silica gel column chromatography gets solid product.Following particular compound is all synthetic by same procedure.
5-(5-(2,4-benzyl dichloride sulfenyl)-4-phenyl-4H-1,2,4-triazole-3-yl)-4-methyl isophthalic acid, 2,3-thiadiazoles (Ia): white crystal, productive rate 73.5%, fusing point 102-103 ℃;
1H NMR (CDCl
3, 400 MHz), δ: 3.07 (s, 3H, Het-Me), 4.61 (s, 2H, SCH
2), 7.14-7.22 (m, 4H, ArH), 7.35-7.40 (m, 2H, ArH), 7.56-7.60 (m, 1H, ArH), 7.64-7.66 (m, 1H, ArH). MS (ESI), m/z:435 (M+1). Elemental anal. (%), calculated:C, 49.77; H, 3.02; N, 16.12; Found:C, 49.98; H, 3.12; N, 16.09.
5-(5-(benzylthio-)-4-phenyl-4H-1,2,4-triazole-3-yl)-4-methyl isophthalic acid, 2,3-thiadiazoles (Ib): white crystal, productive rate 75.0%, fusing point 120-121 ℃;
1H NMR (CDCl
3, 400 MHz), δ: 3.07 (s, 3H, Het-Me), 4.63 (s, 2H, SCH
2), 7.08 (d,
J=7.99Hz, 2H, ArH), 7.28-7.32 (m, 3H, ArH), 7.36-7.38 (m, 2H, ArH), 7.54 (t,
J=8.00Hz, 2H, ArH), 7.64 (t,
J=7.38Hz, 1H, ArH). MS (ESI), m/z:366 (M+1). Elemental anal. (%), calculated:C, 59.15; H, 4.14; N, 19.16; Found:C, 58.89; H, 4.43; N, 19.32.
5-(5-(4-fluorine benzylthio-)-4-phenyl-4H-1,2,4-triazole-3-yl)-4-methyl isophthalic acid, 2,3-thiadiazoles (Ic): white crystal, productive rate 82.2%, fusing point 88-89 ℃;
1H NMR (CDCl
3, 400 MHz), δ: 3.06 (s, 3H, Het-Me), 4.51 (s, 2H, SCH
2), 6.97 (d,
J=8.65Hz, 2H, ArH), 7.13 (d,
J=7.30Hz, 2H, ArH), 7.36-7.39 (m, 2H, ArH), 7.57 (t,
J=8.05Hz, 2H, ArH), 7.65 (t,
J=7.47Hz, 1H, ArH). MS (ESI), m/z:384 (M+1). Elemental anal. (%), calculated:C, 56.38; H, 3.68; N, 18.26; Found:C, 56.12; H, 3.43; N, 18.32.
5-(5-(3-benzyl chloride sulfenyl)-4-phenyl-4H-1,2,4-triazole-3-yl)-4-methyl isophthalic acid, 2,3-thiadiazoles (Id): white crystal, productive rate 85.9%, fusing point 101-102 ℃;
1H NMR (CDCl
3, 400 MHz), δ: 3.04 (s, 3H, Het-Me), 4.47 (s, 2H, SCH
2), 7.10 (d,
J=7.60Hz, 2H, ArH), 7.21-7.28 (m, 3H, ArH), 7.36 (s, 1H, ArH), 7.56 (t,
J=7.25Hz, 2H, ArH), 7.65 (t,
J=7.18Hz, 1H, ArH). MS (ESI), m/z:400 (M+1). Elemental anal. (%), calculated:C, 54.06; H, 3.53; N, 17.51; Found:C, 54.33; H, 3.63; N, 17.67.
5-(5-(3-fluorine benzylthio-)-4-phenyl-4H-1,2,4-triazole-3-yl)-4-methyl isophthalic acid, 2,3-thiadiazoles (Ie): white crystal, productive rate 88.4%, fusing point 98-99 ℃;
1H NMR (CDCl
3, 400 MHz), δ: 3.06 (s, 3H, Het-Me), 4.52 (s, 2H, SCH
2), 6.97 (t,
J=8.25Hz, 1H, ArH), 7.09-7.24 (m, 4H, ArH), 7.56 (t,
J=7.86Hz, 2H, ArH), 7.63-7.69 (m, 2H, ArH). and MS (ESI), m/z:384 (M+1). Elemental anal. (%), calculated:C, 56.38; H, 3.68; N, 18.26; Found:C, 56.75; H, 3.63; N, 18.49.
5-(5-(2-fluorine benzylthio-)-4-phenyl-4H-1,2,4-triazole-3-yl)-4-methyl isophthalic acid, 2,3-thiadiazoles (If): white crystal, productive rate 77.9%, fusing point 104-105 ℃;
1H NMR (CDCl
3, 400 MHz), δ: 3.05 (s, 3H, Het-Me), 4.50 (s, 2H, SCH
2), 7.05 (d,
J=7.70Hz, 2H, ArH), 7.17-7.32 (m, 4H, ArH), 7.52 (t,
J=8.09Hz, 2H, ArH), 7.61 (t,
J=6.97Hz, 1H, ArH). MS (ESI), m/z:384 (M+1). Elemental anal. (%), calculated:C, 56.38; H, 3.68; N, 18.26; Found:C, 56.13; H, 3.77; N, 18.34.
5-(5-(4-methyl benzylthio-)-4-phenyl-4H-1,2,4-triazole-3-yl)-4-methyl isophthalic acid, 2,3-thiadiazoles (Ig): white crystal, productive rate 85.7%, fusing point 115-116 ℃;
1H NMR (CDCl
3, 400 MHz), δ: 2.33 (s, 3H, Ar-Me), 3.06 (s, 3H, Het-Me), 4.55 (s, 2H, SCH
2), 7.02 (d,
J=7.31Hz, 2H, ArH), 7.05-7.22 (m, 3H, ArH), 7.29 (d,
J=7.45Hz, 1H, ArH), 7.52 (t,
J=7.98Hz, 2H, ArH), 7.62 (t,
J=7.47Hz, 1H, ArH). MS (ESI), m/z:380 (M+1). Elemental anal. (%), calculated:C, 60.13; H, 4.52; N, 18.45; Found:C, 59.89; H, 4.67; N, 18.60.
5-(5-(4-benzyl ethyl sulfenyl)-4-phenyl-4H-1,2,4-triazole-3-yl)-4-methyl isophthalic acid, 2,3-thiadiazoles (Ih): white crystal, productive rate 88.9%, fusing point 135-136 ℃;
1H NMR (CDCl
3, 400 MHz), δ: 1.28 (t, 3H, Me), 2.63 (q, 2H, Ar-CH
2), 3.06 (s, 3H, Het-Me), 4.55 (s, 2H, SCH
2), 7.06-7.21 (m, 5H, ArH), 7.51-7.62 (m, 4H, ArH). MS (ESI), m/z:394 (M+1). Elemental anal. (%), calculated:C, 61.04; H, 4.87; N, 17.80; Found:C, 60.99; H, 4.97; N, 17.56.
5-(5-(rosickyite base)-4-phenyl-4H-1,2,4-triazole-3-yl)-4-methyl isophthalic acid, 2,3-thiadiazoles (Ii): white crystal, productive rate 58.6%, fusing point 106-107 ℃;
1H NMR (CDCl
3, 400 MHz), δ: 1.03 (t, 3H, Me), 1.79-1.86 (m, 2H, CH
3C
H 2), 3.06 (s, 3H, Het-Me), 3.30 (t, 3H, CH
3CH
2C
H 2), 4.55 (s, 2H, SCH
2), 7.23-7.25 (m, 2H, ArH), 7.58-7.68 (m, 3H, ArH). MS (ESI), m/z:318 (M+1). Elemental anal. (%), calculated:C, 52.97; H, 4.76; N, 22.06; Found:C, 52.76; H, 4.67; N, 21.96.
5-(5-(2-benzyl chloride sulfenyl)-4-phenyl-4H-1,2,4-triazole-3-yl)-4-methyl isophthalic acid, 2,3-thiadiazoles (2j): white crystal, productive rate 84.5%, fusing point 138-139 ℃;
1H NMR (CDCl
3, 400 MHz), δ: 3.06 (s, 3H, Het-Me), 4.49 (s, 2H, SCH
2), 7.10 (d,
J=7.16Hz, 2H, ArH), 7.22-7.25 (m, 1H, ArH), 7.27-7.29 (m, 1H, ArH), 7.37 (s, 1H, ArH), 7.57 (t,
J=8.00Hz, 2H, ArH), 7.66 (d,
J=7.58Hz, 1H, ArH). MS (ESI), m/z:400 (M+1). Elemental anal. (%), calculated:C, 54.06; H, 3.53; N, 17.51; Found:C, 53.89; H, 3.55; N, 17.78.
The fungicidal activity test
For studying thing: cucumber (Cucumis
SativusL
.), kind is: the close thorn in Xintai City.
Envrionment conditions: 2 cotyledon periods of cucumber seedling.
Test medicine and treatment dosage: each sample is all established an experimental concentration 500mg/L.
Strains tested: the Cucumber Target Leaf Spot bacterium, the cucumber bacterial angular leaf spot bacterium, cucumber didymella bryoniae, bacterium of downy mildew of cucumber, cucumber sclerotiorum, above-mentioned bacterial strains are all from vegetable or flower institute of the Chinese Academy of Agricultural Sciences.
3 repetitions are established in all processing respectively, repeat 10 young plants at every turn, adopt random alignment in the greenhouse.
Dispenser, vaccination ways: reagent agent and contrast medicament are prepared by experimental concentration respectively, the fine morning reagent agent and contrast medicament are evenly sprayed on cucumber cotyledons, inoculate pathogenic bacteria after 2 hours, moisturizing is cultivated.
Wait to contrast abundant morbidity " Invest, Then Investigate " disease index and calculate prevention effect, the results are shown in Table 1.
Table 1The live body fungicidal activity of target compound
| Numbering | Cucumber Target Leaf Spot | Cucumber bacterial angular leaf spot | The climing rot of cucumber | Cucumber downy mildew | Cucumber timberrot |
| Ia | 72.97 | -1.71 | 27.40 | 50.34 | -26.94 |
| Ib | 93.19 | 60.67 | 45.41 | 54.51 | 12.46 |
| Ic | 82.77 | 55.08 | 52.86 | 44.40 | -4.31 |
| Id | 82.30 | 53.92 | 50.37 | 39.15 | 33.97 |
| Ie | 46.90 | 36.71 | 52.32 | 71.03 | 10.29 |
| If | 75.93 | 17.59 | 33.01 | 52.88 | 13.41 |
| Ig | 84.96 | 47.16 | 37.73 | 68.79 | -45.42 |
| Ih | 70.17 | 11.49 | 18.21 | 19.65 | -15.25 |
| Ii | 75.22 | 48.20 | 42.93 | 42.25 | 17.17 |
Claims (5)
1. the thiadiazole compound shown in the formula I,
In the formula I: R is C1-C4 alkyl or substituted-phenyl, and the substituting group of described substituted-phenyl is selected from hydrogen, C1-C4 alkyl, halogen.
2. thiadiazole compound as claimed in claim 1 is characterized in that substituent R is to Chloro-O-Phenyl, a chloro-phenyl-, and adjacent fluorophenyl, a fluorophenyl, to fluorophenyl, p-methylphenyl, to ethylphenyl, 2,4 dichloro benzene base, ethyl.
3. the method for preparing claim 1 or 2 described thiadiazole compounds, it comprises the steps: formula (II) compound and formula III compound are mixed with organic solvent, under the effect of alkaline matter, 0 ~ 25 ℃ of stirring reaction, TLC follows the tracks of reaction, after reacting completely, reaction solution is placed frozen water, separate out solid, filter, filter cake carries out silica gel column chromatography or carries out recrystallization with recrystallization solvent, the thiadiazole compound shown in the acquisition formula (I);
Described recrystallization solvent is one or more in sherwood oil, ethyl acetate, normal hexane or the ethanol;
In described organic solvent DMF, tetrahydrofuran (THF), Isosorbide-5-Nitrae-dioxane or the acetone one or more;
Described alkaline matter is one or more in salt of wormwood, sodium bicarbonate, sodium hydroxide, potassium hydroxide or the sodium hydride;
The mol ratio of formula (II) compound and formula (III) compound and alkaline matter is 1:1.0 ~ 1.5:1.0 ~ 1.5, and the organic solvent volumetric usage is counted 2-10ml/mmol with the amount of substance of formula (II) compound;
Described in the definition such as claim 1 or 2 of R, X is halogen among formula (I), (II).
4. the application of thiadiazole compound claimed in claim 1 in control Cucumber Target Leaf Spot, cucumber bacterial angular leaf spot, the climing rot of cucumber, cucumber downy mildew, cucumber timberrot.
5. sterilant contains acceptable carrier on claim 1 or 2 described thiadiazole compounds and at least a agricultural chemicals.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103193769A (en) * | 2013-04-15 | 2013-07-10 | 南开大学 | 4-methyl-1,2,3-thiadiazole-5-triazole compound as well as preparation method and use thereof |
| CN103626737A (en) * | 2013-12-10 | 2014-03-12 | 浙江工业大学 | Application of triazole compound containing pyridine as bactericide |
| CN104230914A (en) * | 2014-08-26 | 2014-12-24 | 盐城师范学院 | 1,2,4-triazole compounds and preparation method thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1927859A (en) * | 2005-09-08 | 2007-03-14 | 沈阳化工研究院 | Substituted oxdiazole or triazole thioketone compounds, preparation and application thereof |
| CN101003533A (en) * | 2007-01-12 | 2007-07-25 | 南开大学 | Derivative of thiadiazoles containing cyclo oxdiazole, synthetic method, and biological activity |
| CN102276596A (en) * | 2011-06-23 | 2011-12-14 | 浙江工业大学 | Thiadiazole compound as well as preparation and application thereof |
| WO2012080729A2 (en) * | 2010-12-14 | 2012-06-21 | Electrophoretics Limited | CASEIN KINASE 1δ (CK1δ) INHIBITORS |
-
2012
- 2012-09-05 CN CN201210324814.1A patent/CN102850341B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1927859A (en) * | 2005-09-08 | 2007-03-14 | 沈阳化工研究院 | Substituted oxdiazole or triazole thioketone compounds, preparation and application thereof |
| CN101003533A (en) * | 2007-01-12 | 2007-07-25 | 南开大学 | Derivative of thiadiazoles containing cyclo oxdiazole, synthetic method, and biological activity |
| WO2012080729A2 (en) * | 2010-12-14 | 2012-06-21 | Electrophoretics Limited | CASEIN KINASE 1δ (CK1δ) INHIBITORS |
| CN102276596A (en) * | 2011-06-23 | 2011-12-14 | 浙江工业大学 | Thiadiazole compound as well as preparation and application thereof |
Non-Patent Citations (3)
| Title |
|---|
| AGATA SIWEK，等: ""Study of Direction of Cyclization of 1-Azolil-4-Aryl/Alkyl-Thiosemicarbazides"", 《HETEROATOM CHEMISTRY》 * |
| AMIR REZA JALILIAN，等: ""Synthesis and in Vitro Antifungal and Cytotoxicity Evaluation of Thiazolo-4H-1,2,4-triazoles and 1,2,3-Thiadiazolo-4H-1,2,4-triazoles"", 《ARCH. PHARM. PHARM. MED. CHEM.》 * |
| XING-HAI LIU，等: ""Synthesis, structure, and biological activity of novel (oxdi/tri)azoles derivatives containing 1,2,3-thiadiazole or methyl moiety"", 《MOL DIVERS》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103193769A (en) * | 2013-04-15 | 2013-07-10 | 南开大学 | 4-methyl-1,2,3-thiadiazole-5-triazole compound as well as preparation method and use thereof |
| CN103626737A (en) * | 2013-12-10 | 2014-03-12 | 浙江工业大学 | Application of triazole compound containing pyridine as bactericide |
| CN103626737B (en) * | 2013-12-10 | 2015-10-28 | 浙江工业大学 | A kind of application of triazole class compounds as sterilant containing pyridine |
| CN104230914A (en) * | 2014-08-26 | 2014-12-24 | 盐城师范学院 | 1,2,4-triazole compounds and preparation method thereof |
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