CN102850342A - Oxdiazole compound containing thiadiazole, preparation method and applications thereof - Google Patents

Oxdiazole compound containing thiadiazole, preparation method and applications thereof Download PDF

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CN102850342A
CN102850342A CN2012103248300A CN201210324830A CN102850342A CN 102850342 A CN102850342 A CN 102850342A CN 2012103248300 A CN2012103248300 A CN 2012103248300A CN 201210324830 A CN201210324830 A CN 201210324830A CN 102850342 A CN102850342 A CN 102850342A
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compound
cucumber
thiadiazoles
oxadiazole
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CN102850342B (en
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武宏科
童建颖
孙娜波
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Zhejiang University of Technology ZJUT
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Abstract

The present invention relates to an oxdiazole compound containing thiadiazole, and a preparation method thereof. The compound of the present invention has a structure represented by a formula (I), wherein R is a substituted phenyl, the benzene ring on the substituted phenyl is monosubstituted or polysubstituted, the substituted group is independently selected from one of hydrogen, C1-C4 alkyl, C1-C4 alkoxy and halogen. The 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

A kind of containing thiadiazoles oxadiazole compounds and preparation and application thereof
technical field
The present invention relates to a kind of is 2-(4-methyl isophthalic acid, 2,3-thiadiazoles-5-yl)-5-(replacement benzylthio-)-1,3 containing thiadiazoles oxadiazole compounds, 4-oxadiazole 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, take again nitrogen heterocyclic ring as main.1,3,4-oxadiazole compounds also has very important biological activity, comprises anti-inflammatory, anticancer, antiviral, bacteriostasis and herbicides isoreactivity.As synthetic 2-substituted pyrazolecarboxylic-5-methylthio group-1,3, the 4-oxadiazole shows good inhibition activity to Rhizoctonia solani Kuhn when 100 mg/L; 2-methyl-5-replaces benzylthio--1,3, and the 4-oxadiazole has inhibition preferably to rape under 100ppm.1,2,3 thiadiazole compounds are development in recent years classes more rapidly, 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 are also had to prevention effect preferably as brown spot, bacterial leaf-blight, banded sclerotial blight and sesame leaf rot etc.And the induced resistance of plant activiator Bion(BTH of Novartis Co.,Ltd's exploitation).
Figure 2012103248300100002DEST_PATH_IMAGE001
Yet, there is not yet relevant 2-(4-methyl isophthalic acid, 2,3-thiadiazoles-5-yl)-5-(replacement benzylthio-)-1,3, the bibliographical information of the synthetic and bioactivity research of 4-oxadiazole derivative.
summary of the invention
The object of the invention is to provide a kind of 2-(4-methyl isophthalic acid, 2,3-thiadiazoles-5-yl) with fungicidal activity-5-(replacement benzylthio-)-1,3,4-oxadiazole derivative and preparation method thereof and application.
The object of the present invention is achieved like this:
Shown in formula (I) containing thiadiazoles oxadiazole compounds:
Figure 5154DEST_PATH_IMAGE002
（I）
In formula (I): R is substituted-phenyl, and described replacement is selected from hydrogen, C1-C4 alkyl, C1-C4 alkoxyl group and 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, under the existence of alkaline matter, 0 ~ 25 ℃ of (preferably 25 ℃) stirring reaction, TLC follows the tracks of reaction, and (sherwood oil and the ethyl acetate mixture of volume ratio 1:1 ~ 5 of take is developping agent, following the tracks of raw material point disappears for reacting completely), after reacting completely, reaction solution is placed in to frozen water, separate out solid, filter, filtrate is carried out silica gel column chromatography, and (sherwood oil that the volume ratio of take is 5:1 and ethyl acetate mixture are eluent, collect the elutriant containing target components, dry) or carry out recrystallization with recrystallization solvent, shown in acquisition formula (I) containing thiadiazoles oxadiazole compounds,
Recrystallization solvent is one or more in sherwood oil, ethyl acetate, normal hexane or ethanol, preferably the mixing solutions of sherwood oil and ethyl acetate;
Organic solvent is one or more in DMF, tetrahydrofuran (THF), Isosorbide-5-Nitrae-dioxane or acetone, is preferably DMF (DMF);
Alkaline matter is one or more in salt of wormwood, sodium bicarbonate, sodium hydroxide, potassium hydroxide or 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, preferably 4ml/mmol.
Figure DEST_PATH_IMAGE003
In formula (I) and formula (III): as previously mentioned, X is halogen or tosic acid ester group in the definition of R.
The present invention also provides the application in control Cucumber Target Leaf Spot, cucumber bacterial angular leaf spot, the climing rot of cucumber, cucumber downy mildew, cucumber timberrot containing thiadiazoles oxadiazole compound shown in formula (I).
The present invention also provides and contains the sterilant containing thiadiazoles oxadiazole compound shown in formula (I), and it also comprises acceptable auxiliary agent at least one agricultural chemicals.
Compared with prior art, beneficial effect of the present invention is mainly reflected in: the invention provides a kind of its preparation method and application containing thiadiazoles oxadiazole compounds and intermediate, this compound is the new compound with fungicidal activity, for the research and development of novel pesticide provide the foundation.
embodiment
Below in conjunction with specific embodiment, the present invention is described further, but protection scope of the present invention is not limited in this:
It is of the present invention that containing thiadiazoles oxadiazole compounds (I), method is synthetic as follows:
In 25 mL round-bottomed flasks, add 2 mmol Compound I I, 2 mmol to replace the K of benzyl chloride, 8mL DMF and 2.4mmol 2cO 3, stirring at room, TLC detection reaction progress.After completion of the reaction, in reaction solution impouring 30mL frozen water, separate out solid, filter, precipitation, silica gel column chromatography, obtain solid product.
Embodiment 1
2-(4-methyl isophthalic acid, 2,3-thiadiazoles-5-yl)-5-(2,4-benzyl dichloride sulfenyl)-1,3,4-oxadiazole (Ia): white crystal, productive rate 84%, fusing point 85-86 ℃; 1h NMR (CDCl 3, 400 MHz), δ: 3.06 (s, 3H, Het-Me), 4.60 (s, 2H, SCH 2), 7.22 (d, j=8.49Hz, 1H, ArH), 7.44 (s, 1H, ArH), 7.61 (d, j=8.27Hz, 1H, ArH). MS (ESI), m/z:360 (M+1). Elemental anal. (%), calculated:C, 40.12; H, 2.24; N, 15.60; Found:C, 39.88; H, 2.55; N, 15.79.
Embodiment 2
2-(4-methyl isophthalic acid, 2,3-thiadiazoles-5-yl)-5-(3-benzyl chloride sulfenyl)-1,3,4-oxadiazole (Ib): white crystal, productive rate 88%, fusing point 88-89 ℃; 1h NMR (CDCl 3, 400 MHz), δ: 3.06 (s, 3H, Het-Me), 4.51 (s, 2H, SCH 2), 7.30 (s, 2H, ArH), 7.34-7.39 (m; 1H, ArH), 7.47 (s, 1H; ArH). MS (ESI), m/z:326 (M+1). Elemental anal. (%), calculated:C, 44.37; H, 2.79; N, 17.25; Found:C, 44.67; H, 2.85; N, 17.43.
Embodiment 3
2-(4-methyl isophthalic acid, 2,3-thiadiazoles-5-yl)-5-(3-fluorine benzylthio-)-1,3,4-oxadiazole (Ic): white crystal, productive rate 79%, fusing point 63-64 ?c; 1h NMR (CDCl 3, 400 MHz), δ: 3.06 (s, 3H, Het-Me), 4.53 (s, 2H, SCH 2), 7.04 (t, j=7.46Hz, 1H, ArH), 7.19 (d, j=9.27Hz, 1H, ArH), 7.29-7.35 (m, 2H, ArH). and MS (ESI), m/z:309 (M+1). Elemental anal. (%), calculated:C, 46.74; H, 2.94; N, 18.17; Found:C, 46.45; H, 3.12; N, 18.44.
Embodiment 4
2-(4-methyl isophthalic acid, 2,3-thiadiazoles-5-yl)-5-(2-benzyl chloride sulfenyl)-1,3,4-oxadiazole (Id): white crystal, productive rate 81%, fusing point 98-99 ℃; 1h NMR (CDCl 3, 400 MHz), δ: 3.06 (s, 3H, Het-Me), 4.65 (s, 2H, SCH 2), 7.26-7.30 (m, 2H, ArH), 7.41 (d, j=7.45Hz, 1H, ArH), 7.63 (d, j=7.14Hz, 1H, ArH). MS (ESI), m/z:326 (M+1). Elemental anal. (%), calculated:C, 44.37; H, 2.79; N, 17.25; Found:C, 44.64; H, 2.99; N, 17.01.
Embodiment 5
2-(4-methyl isophthalic acid, 2,3-thiadiazoles-5-yl)-5-(2-fluorine benzylthio-)-1,3,4-oxadiazole (Ie): white crystal, productive rate 85%, fusing point 78-79 ℃; 1h NMR (CDCl 3, 400 MHz), δ: 3.06 (s, 3H, Het-Me), 4.58 (s, 2H, SCH 2), 7.07-7.14 (m, 2H, ArH), 7.29-7.33 (m, 1H, ArH), 7.55 (t, j=8.20Hz, 1H, ArH). MS (ESI), m/z:309 (M+1). Elemental anal. (%), calculated:C, 46.74; H, 2.94; N, 18.17; Found:C, 46.88; H, 3.12; N, 18.43.
Embodiment 6
2-(4-methyl isophthalic acid, 2,3-thiadiazoles-5-yl)-5-(2-methyl benzylthio-)-1,3,4-oxadiazole (If): white crystal, productive rate 83%, fusing point 79-80 ℃; 1h NMR (CDCl 3, 400 MHz), δ: 2.45 (s, 3H, Ar-Me), 3.06 (s, 3H, Het-Me), 4.59 (s, 2H, SCH 2), 7.8-7.23 (m, 2H, ArH), 7.29-7.34 (m, 1H, ArH), 7.42 (d, j=6.11Hz, 1H, ArH). MS (ESI), m/z:305 (M+1). Elemental anal. (%), calculated:C, 51.30; H, 3.97; N, 18.41; Found:C, 51.55; H, 3.87; N, 18.49.
Embodiment 7
2-(4-methyl isophthalic acid, 2,3-thiadiazoles-5-yl)-5-(4-fluorine benzylthio-)-1,3,4-oxadiazole (Ig): white crystal, productive rate 77%, fusing point 84-85 ℃; 1h NMR (CDCl 3, 400 MHz), δ: 2.45 (s, 3H, Ar-Me), 3.06 (s, 3H, Het-Me), 4.52 (s, 2H, SCH 2), 7.06 (t, j=8.55Hz, 2H, ArH), 7.46 (d, j=5.76Hz, 2H, ArH). MS (ESI), m/z:305 (M+1). Elemental anal. (%), calculated:C, 46.74; H, 2.94; N, 18.17; Found:C, 46.88; H, 3.06; N, 17.99.
Embodiment 8
2-(4-methyl isophthalic acid, 2,3-thiadiazoles-5-yl)-5-(benzylthio-)-1,3,4-oxadiazole (Ih): white crystal, productive rate 88%, fusing point 72-73 ℃; 1h NMR (CDCl 3, 400 MHz), δ: 3.05 (s, 3H, Het-Me), 4.55 (s, 2H, SCH 2), 7.30-7.37 (m, 3H, ArH), 7.46 (d, j=7.21Hz, 2H, ArH). MS (ESI), m/z:291 (M+1). Elemental anal. (%), calculated:C, 49.64; H, 3.47; N, 19.30; Found:C, 50.01; H, 3.78; N, 19.12.
Embodiment 9
2-(4-methyl isophthalic acid, 2,3-thiadiazoles-5-yl)-5-(4-methoxybenzyl sulfenyl)-1,3,4-oxadiazole (Ii): white crystal, productive rate 79%, fusing point 56-57 ℃; 1h NMR (CDCl 3, 400 MHz), δ: 3.05 (s, 3H, Het-Me), 3.80 (s, 3H, OMe), 4.52 (s, 2H, SCH 2), 6.87 (d, j=8.41Hz, 2H, ArH), 7.41 (d, j=8.46Hz, 2H, ArH). MS (ESI), m/z:321 (M+1). Elemental anal. (%), calculated:C, 48.73; H, 3.78; N, 17.49; Found:C, 48.78; H, 3.99; N, 17.54.
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, the cucumber didymella bryoniae, bacterium of downy mildew of cucumber, cucumber sclerotiorum, above-mentioned bacterial strains is 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 greenhouse.
Dispenser, vaccination ways: reagent agent and contrast medicament are prepared by experimental concentration respectively, the morning reagent agent and contrast medicament are evenly sprayed on cucumber cotyledons in fine day, after 2 hours, inoculate pathogenic bacteria, moisturizing is cultivated.
Wait to contrast abundant morbidity " Invest, Then Investigate " disease index and calculate prevention effect, the results are shown in Table 1.
Figure 797660DEST_PATH_IMAGE004
Figure DEST_PATH_IMAGE005
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 77.66 68.08 -2.73 41.78 36.93
Ib 53.68 38.02 19.13 35.97 12.98
Ic 84.55 53.30 59.52 68.43 21.16
Id 92.77 58.22 48.17 53.13 -10.26
Ie 94.64 47.98 56.81 53.13 -21.48
If 88.12 53.27 26.02 45.39 3.05
Ig 72.35 14.78 31.99 46.24 16.48
Ih 72.72 65.59 23.72 42.75 32.51
Ii 64.26 32.62 -11.66 59.56 0.81

Claims (5)

  1. Shown in a formula (I) containing the oxadiazole compounds of thiadiazoles,
    In formula (I), R is substituted-phenyl, and described replacement is selected from hydrogen, C1-C4 alkyl, C1-C4 alkoxyl group and halogen.
  2. 2. the oxadiazole compounds containing thiadiazoles as claimed in claim 1, is characterized in that in described formula (I), R is Chloro-O-Phenyl, a chloro-phenyl-, and adjacent fluorophenyl, a fluorophenyl, to fluorophenyl, o-methyl-phenyl-, phenyl, 2,4 dichloro benzene base, p-methoxyphenyl.
  3. 3. prepare the described method containing thiadiazoles oxadiazole compound of claim 1 or 2, 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 in to frozen water, separates out solid, filter, filter cake carries out silica gel column chromatography or carries out recrystallization with recrystallization solvent, shown in acquisition formula (I) containing thiadiazoles oxadiazole compounds;
    Described recrystallization solvent is one or more in sherwood oil, ethyl acetate, normal hexane or ethanol;
    One or more in described organic solvent DMF, tetrahydrofuran (THF), Isosorbide-5-Nitrae-dioxane or acetone;
    Described alkaline matter is one or more in salt of wormwood, sodium bicarbonate, sodium hydroxide, potassium hydroxide or sodium hydride;
    The ratio of the amount of substance 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;
    Figure 100227DEST_PATH_IMAGE002
    In formula (I), (II), the definition of R is described in claim 1 or 2, and X is halogen.
  4. 4. the application of the oxadiazole compound containing thiadiazoles as claimed in claim 1 in preparation control Cucumber Target Leaf Spot, cucumber bacterial angular leaf spot, the climing rot of cucumber, cucumber downy mildew, cucumber timberrot sterilant.
  5. 5. sterilant, contain claim 1 or 2 described containing acceptable auxiliary agent on thiadiazoles oxadiazole compound and at least one agricultural chemicals.
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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102838593A (en) * 2012-10-08 2012-12-26 贵州大学 2-(4-methyl-1,2,3-thiadiazole)-5-(substituent)-1,3,4-oxa(thia)diazole derivative and application thereof
CN103896934A (en) * 2014-02-28 2014-07-02 盐城工学院 Thiadiazole-containing oxadiazole compound as well as preparation method and application thereof
CN106243101A (en) * 2016-07-28 2016-12-21 浙江工业大学 A kind of 1,3,4 thiadiazoles sulfide derivatives and its preparation method and application
CN114989155A (en) * 2021-03-01 2022-09-02 河北农业大学 1,3, 4-oxadiazole thioether derivative and preparation method and application thereof

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CN102276596A (en) * 2011-06-23 2011-12-14 浙江工业大学 Thiadiazole compound as well as preparation and application thereof

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CN102276596A (en) * 2011-06-23 2011-12-14 浙江工业大学 Thiadiazole compound as well as preparation and application thereof

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Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102838593A (en) * 2012-10-08 2012-12-26 贵州大学 2-(4-methyl-1,2,3-thiadiazole)-5-(substituent)-1,3,4-oxa(thia)diazole derivative and application thereof
CN103896934A (en) * 2014-02-28 2014-07-02 盐城工学院 Thiadiazole-containing oxadiazole compound as well as preparation method and application thereof
CN106243101A (en) * 2016-07-28 2016-12-21 浙江工业大学 A kind of 1,3,4 thiadiazoles sulfide derivatives and its preparation method and application
CN106243101B (en) * 2016-07-28 2019-05-24 浙江工业大学 A kind of 1,3,4- thiadiazoles sulfide derivative and its preparation method and application
CN114989155A (en) * 2021-03-01 2022-09-02 河北农业大学 1,3, 4-oxadiazole thioether derivative and preparation method and application thereof
CN114989155B (en) * 2021-03-01 2024-04-02 河北农业大学 1,3, 4-oxadiazole thioether derivative, and preparation method and application thereof

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