CN101838265A - [5-(Arylmethylideneimino)-1,3,4-thiadiazol-2-yl]thioethylacetate as well as preparation and application thereof - Google Patents
[5-(Arylmethylideneimino)-1,3,4-thiadiazol-2-yl]thioethylacetate as well as preparation and application thereof Download PDFInfo
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Abstract
The invention provides a method for synthesizing [5-(Arylmethylideneimino)-1,3,4-thiadiazol-2-yl]thioethylacetate, which belongs to the technical field of chemical synthesis. 2-amino-5-sulfhydryl-1,3,4-thiadiazol and ethyl chloroacetate are used as the raw material to efficiently and rapidly synthesize an intermediate (5- amino-1,3,4-thiadiazol-2-yl) thioethylacetate in a water phase; and the intermediate is condensed with aromatic aldehyde to obtain the target compound [5-(Arylmethylideneimino)-1,3,4-thiadiazol-2-yl]thioethylacetate with high yield. Results of biological tests show that the compound [5-(Arylmethylideneimino)-1,3,4-thiadiazol-2-yl]thioethylacetate synthesized has good promoting function for the growth of wheat seedlings; as part of compounds has good inhibition to cucumber wilt pathogen and tomato gray mold pathogen, the [5-(Arylmethylideneimino)-1, 3, 4-thiadiazol-2-yl]thioethylacetate can be used as a plant growth regulator and a bacteriostatic agent to be applied in the agricultural production.
Description
Technical field
The invention belongs to technical field of chemical synthesis, relate to a kind of compound [5-(aryl methylene imino-)-1,3,4-thiadiazoles-2-yl] sulphur ethyl acetate and preparation method thereof; The invention still further relates to the application in agricultural of this compound as plant-growth regulator and fungistat.
Background technology
Thiadiazole compound has tangible conjugative effect and aromaticity, shows wide biological activity aspect agricultural chemicals, can make sterilant, weedicide, plant-growth regulator and agrochemical.1,3, the substituting group on 2,5 of the 4-thiadiazoles can participate in numerous chemical reactions, usually is introduced in the pesticide molecule as active group.Therefore, to 1,3, the molecular designing of 4-thiadiazole compound, become a focus of novel pesticide research.1,3, in the 4-thiadiazole heterocyclic, to containing 1,3 of Schiff alkali structure, the research of 4-thiadiazoles derivative is less relatively, but this compounds has good biological activity and good ligancy.And that some contain sulfydryl is substituent 1,3, and the synthetic product of 4-thiadiazoles derivative and chloracetate has good antibacterial activity, and indivedual products also have activity anticancer, the treating pulmonery tuberculosis mycobacterium.According to the sub-superposition theorem of activity, design is synthetic to contain 1,3 of Schiff alkali structure, 4-thiadiazoles ethyl thioglycollic acid ester derivative, and expectation obtains better plant-growth regulator of biological activity and fungistat.
Summary of the invention
The purpose of this invention is to provide a kind of new compound [5-(aryl methylene imino-)-1,3,4-thiadiazoles-2-yl] sulphur ethyl acetate.
The preparation method of sulphur ethyl acetate that another object of the present invention provides a kind of [5-(aryl methylene imino-)-1,3,4-thiadiazoles-2-yl].
A further object of the invention, just provide a kind of [5-(aryl methylene imino-)-1,3,4-thiadiazoles-2-yl] sulphur ethyl acetate as plant-growth regulator and fungistat in application in agriculture.
One, [5-(aryl methylene imino-)-1,3,4-thiadiazoles-2-yl] sulphur ethyl acetate
The structure of The compounds of this invention [5-(aryl methylene imino-)-1,3,4-thiadiazoles-2-yl] sulphur ethyl acetate is as follows:
Two, the preparation of [5-(aryl methylene imino-)-1,3,4-thiadiazoles-2-yl] sulphur ethyl acetate
The synthetic method of The compounds of this invention [5-(aryl methylene imino-)-1,3,4-thiadiazoles-2-yl] sulphur ethyl acetate, be with 2-amino-5-sulfydryl-1,3,4-thiadiazoles and ethyl chloroacetate are raw material, efficient, quick synthetic intermediate (the 5-amino-1 of water, 3,4-thiadiazoles-2-yl) sulphur ethyl acetate, this intermediate again with aromatic aldehyde generation condensation, high yield obtains target compound [5-(aryl methylene imino-)-1,3,4-thiadiazoles-2-yl] the sulphur ethyl acetate.Concrete processing step is as follows:
(1) intermediate (5-amino-1,3,4-thiadiazoles-2-yl) sulphur ethyl acetate is synthetic
At aqueous phase, with 2-amino-5-sulfydryl-1,3,4-thiadiazoles and ethyl chloroacetate react 15～30min with 1: 1～1: 1.5 mol ratio under room temperature, suction filtration, washing and get.
Because 2-amino-5-sulfydryl-1,3, there is the tautomerism of mercaptan-thioketones in 5 sulfydryls in the 4-thiadiazoles molecular structure, under alkaline condition, easily generate stable sulphur negative ion, the S-alkylation takes place, so intermediate (5-amino-1,3,4-thiadiazoles-2-yl) should carry out synthesizing of sulphur ethyl acetate at alkaline aqueous phase.
(2) [5-(aryl methylene imino-)-1,3,4-thiadiazoles-2-yl] sulphur ethyl acetate is synthetic
With the dehydrated alcohol is solvent, is catalyzer with the Glacial acetic acid, with (5-amino-1,3,4-thiadiazoles-2-yl) sulphur ethyl acetate and the aromatic aldehyde mass ratio with 1.4: 1～3.5: 1, in 75～80 ℃ of following stirring and refluxing 2～3h; Reaction boils off solvent after finishing, and cooling gets pure product [5-(aryl methylene imino-)-1,3,4-thiadiazoles-2-yl] sulphur ethyl acetate with the dehydrated alcohol recrystallization.
Wherein aromatic aldehyde is furfural, salicylaldhyde, Vanillin or terephthalaldehyde, and corresponding product is respectively 2a, 2b, 2c, 2d.
The amount of described catalyzer Glacial acetic acid is 0.5～1% of an aromatic aldehyde molar weight.
The amount of dehydrated alcohol is suitable for reactant fully is dissolved as.
Its synthesis route is as follows:
Synthesis route of the present invention have the reaction conditions gentleness, efficient, easy to operate, save the energy, pollute advantages such as few, be a kind of synthetic 1,3,4-thiadiazoles ethyl thioglycollic acid ester compound perfect method.
Three, the sign of [5-(aryl methylene imino-)-1,3,4-thiadiazoles-2-yl] sulphur ethyl acetate
The sign of [5-(aryl methylene imino-)-1,3,4-thiadiazoles-2-yl] sulphur ethyl acetate product of the present invention's preparation is as follows:
2a: yellow needle-like crystal, productive rate 81%, m.p.124～126 ℃;
1H NMR (CDCl
3, 400MHz) δ: 1.30～1.32 (t, 3H, CH
3), 4.13 (s, 2H, SCH
2), 4.20～4.27 (q, 2H, OCH
2), 6.65～7.74 (m, 3H, Furyl), 8.77 (s, 1H, CH=N); IR (KBr) v:1600 (C=O), 1504 (CH=N), 1379 (SCH
2) cm
-1.Anal.calcd for C
11H
11N
3O
3S
2: C 44.43, and H 3.73, and N 14.13; FoundC 44.57, and H 3.99, and N 14.01.
2b: yellow crystals, productive rate 79%, m.p.91～93 ℃;
1H NMR (CDCl
3, 400MHz) δ: 1.27～1.31 (t, 3H, CH
3), 3.92 (s, 2H, SCH
2), 4.15～4.24 (q, 2H, OCH
2), 6.98～7.51 (m, 4H, ArH), 9.04 (s, 1H, CH=N), 11.76 (s, 1H, OH); IR (KBr) v:1624 (C=O), 1520 (CH=N), 1364 (SCH
2) cm
-1.Anal.calcd for C
13H
13N
3O
3S
2: C 48.28, H4.05, and N 12.99; Found C 48.13, H 3.88, and N 13.06.
2c: yellow crystals, productive rate 83%, m.p.101～103 ℃;
1H NMR (CDCl
3, 400MHz) δ: 1.30～1.32 (t, 3H, CH
3), 4.00 (s, 3H, OCH
3), 4.16 (s, 2H, SCH
2), 4.21～4.26 (q, 2H, OCH
2), 7.00～7.68 (m, 3H, ArH), 8.65 (s, 1H, CH=N), 9.83 (s, 1H, OH); IR (KBr) v:1575 (C=O), 1523 (CH=N), 1384 (SCH
2) cm
-1.Anal.calcd forC
14H
15N
3O
4S
2: C 47.58, and H 4.28, and N 11.89; Found C 47.86, H 4.07, and N 11.91.
2d: yellow crystals, productive rate 87%, m.p.230～231 ℃;
1H NMR (CDCl
3, 400MHz) δ: 1.29～1.33 (t, 6H, CH
3), 4.18 (s, 4H, SCH
2), 4.24～4.29 (q, 4H, OCH
2), 8.03～8.16 (m, 4H, ArH), 8.94 (s, 2H, CH=N); IR (KBr) v:1607 (C=O), 1507 (CH=N), 1363 (SCH
2) cm
-1.Anal.calcd for C
20H
20N
6O
4S
4: C 44.76, H 3.76., and N 15.66; FoundC 44.83, and H 3.68, and N 15.56.
The Spectrum Analysis of [5-(aryl methylene imino-)-1,3,4-thiadiazoles-2-yl] sulphur ethyl acetate: in the infrared spectra of compound 2a, 2b, 2c, 2d, at 1575～1624cm
-1Between the strong absorption characteristic peak that occurs be the C=O stretching vibration peak.At 1504～1523cm
-1Between the absorption peak of CH=N medium tenacity appears.And compound is at 1363～1384cm
-1Between SCH appears
2Charateristic avsorption band, illustrate the sulfur alkylation reaction taken place;
1In the H NMR spectrum, be that example explanation compound is target product: the methylene radical (SCH that sulphur atom links to each other with 2a
2) unimodal in the appearance of δ 4.13 places, the peak at δ 6.65～7.74 places belongs to the furans ring hydrogen, and the singlet at 8.77 places belongs to CH=N.Spectrum Analysis is consistent with the structure of target compound.
Four, the biological activity test of [5-(aryl methylene imino-)-1,3,4-thiadiazoles-2-yl] sulphur ethyl acetate
With [5-(aryl methylene imino-)-1,3,4-thiadiazoles-2-yl] sulphur ethyl acetate 2a, 2b, 2c, 2d product be made into 100 respectively, 10,1,0.1,0.01,0.001mg/L the solution of concentration adopts plate culture, studies its growth regulating effect to monocotyledons wheat seedling root system and bud.Make blank assay with distilled water, the indolylacetic acid solution of same concentrations is made standard control.Incubated at room temperature wheat seed 6 days is measured the long length of wheat radicle and blastogenesis.Calculate this compounds growth regulating-activity to wheat seedling root system and bud under each concentration with following formula:
A＝(N-N
0)/N
0×100％
A---sample plant growth regulating activity
N---the growth length of wheat root and bud in the solution
N
0---the growth length of wheat root and bud in the distilled water
Inhibition (promotion) rate (%) that compound [5-(aryl methylene imino-)-1,3,4-thiadiazoles-2-yl] sulphur ethyl acetate is long to the monocotyledons wheat root, bud is long sees Table 1.
Table 1 compound 2a, 2b, 2c, 2d regulate data (%) to the growth activity of wheat
Annotate:
aCompound is to the biological activity of wheat malt;
bCompound is to the biological activity of wheat root;
cIAA represents indolylacetic acid
From the data of table 1 as can be seen, compare with indolylacetic acid, compound [5-(aryl methylene imino-)-1,3,4-thiadiazoles-2-yl] sulphur ethyl acetate 2a, 2b, 2c, 2d, growth to wheat when high density shows restraining effect, and the growth to wheat shows fine promoter action when lower concentration.And the growth table to wheat root and bud under 0.01mg/L, 0.001mg/L concentration reveals better promotion activity, and major part obviously is better than indolylacetic acid.Wherein binary derivative 2d promotes wheat to take root, germinate active best when 0.001mg/L concentration, and it promotes that growth rate is respectively 62.6% and 43.0%.Therefore, compound 2a, 2b, 2c, 2d can be used as plant-growth regulator, are applied in agriculture production.
Five, the bacteriostatic activity of [5-(aryl methylene imino-)-1,3,4-thiadiazoles-2-yl] sulphur ethyl acetate test
[5-(aryl methylene imino-)-1,3,4-thiadiazoles-2-yl] sulphur ethyl acetate 2a, 2b, 2c, product are made into 150 respectively, 100,75, the solution of 50mg/L concentration, adopt growth rate method, study its restraining effect cucumber fusarium axysporum and botrytis cinerea.Make blank assay with distilled water, the solvent of same concentrations (trichloromethane) is made standard control.Controlled temperature is 25 ± 1 ℃ in growth cabinet, and dark illumination was alternately cultivated 3 days, measures colony diameter.Calculate this compounds restraining effect to cucumber fusarium axysporum and botrytis cinerea under each concentration with following formula:
A＝(N
0-N)/N
0×100％
A---sample bacteriostatic activity
N
0---colony diameter in the solvent (trichloromethane)
N---colony diameter in the solution
Compound is listed in table 2 to cucumber fusarium axysporum and botrytis cinerea inhibiting rate (%).
Table 2 compound 2a, 2b, 2c, 2d are to cucumber fusarium axysporum and botrytis cinerea inhibiting rate data (%)
Annotate:
aCompound is to the restraining effect of cucumber fusarium axysporum;
bCompound is to the restraining effect of botrytis cinerea
From the data of table 2 as can be seen, compound [5-(aryl methylene imino-)-1,3,4-thiadiazoles-2-yl] sulphur ethyl acetate 2a, 2b, 2c, under 100mg/L, 150mg/L concentration, cucumber fusarium axysporum and botrytis cinerea are shown good inhibition effect.Wherein compound 2a is best to the inhibition activity of cucumber fusarium axysporum and botrytis cinerea, and its maximal percentage inhibition reaches 82.5% and 87.0% respectively.Therefore, compound 2a, 2b, 2c can be used as fungistat, are applied in agriculture production.
Embodiment
Be further detailed below by the preparation and the application of specific embodiment The compounds of this invention.
Embodiment one
1, compound [5-(furfurylidene imino-)-1,3,4-thiadiazoles-2-yl] sulphur ethyl acetate 2a's is synthetic
(1) intermediate (5-amino-1,3,4-thiadiazoles-2-yl) sulphur ethyl acetate 1 is synthetic
Add 5.25mol sodium hydroxide in the 50ml round-bottomed flask, 4ml water is made into the aqueous solution of sodium hydroxide.Add 5mol 2-amino-5-sulfydryl-1,3 again, the 4-thiadiazoles, stirring makes in its aqueous solution that is dissolved in sodium hydroxide fully.After treating dissolving fully, at room temperature add the 7mol ethyl chloroacetate in three batches, reaction process is followed the tracks of with TLC point plate, raw material point disappears behind the 15min, obtains solidliquid mixture, suction filtration, obtain solid, use the 5ml distilled water wash again, suction filtration obtains solid product, ethyl alcohol recrystallization, obtain intermediate (5-amino-1,3,4-thiadiazoles-2-yl) sulphur ethyl acetate 1.
(2) [5-(furfurylidene imino-)-1,3,4-thiadiazoles-2-yl] sulphur ethyl acetate 2a's is synthetic
The compound 1 that in the 50ml round-bottomed flask, adds 5mol, the furfural of 5mol, the catalysis of 0.04ml Glacial acetic acid, the 15ml dehydrated alcohol is a solvent, be heated to 75～80 ℃ of stirring and refluxing 2～3h, reaction boils off solvent after finishing, and cooling gets crude product, the dehydrated alcohol recrystallization, get pure product [5-(furfurylidene imino-)-1,3,4-thiadiazoles-2-yl] sulphur ethyl acetate 2a.Productive rate 81%.
2, compound [5-(furfurylidene imino-)-1,3,4-thiadiazoles-2-yl] sulphur ethyl acetate 2a is as the application of plant-growth regulator
With compound [5-(furfurylidene imino-)-1,3,4-thiadiazoles-2-yl] sulphur ethyl acetate 2a is made into 100,10,1,0.1,0.01, the solution of 0.001mg/L concentration, adopt plate culture, study the sweet growth regulating effect of cultivating No. No. 4 seedlings root and bud of its monocotyledons wheat, make blank assay with distilled water, the indolylacetic acid solution of same concentrations is made standard control.Incubated at room temperature wheat seed 6 days is measured the long length of wheat radicle and blastogenesis.Calculate this compounds growth regulating-activity to rape, wheat seedling root system and bud under each concentration with following formula: A=(N-N
0)/N
0* 100%, wherein: A is the sample plant growth regulating activity, and N is the growth length of rape, wheat root and bud in the solution, N
0Growth length for rape, wheat root and bud in the distilled water.Test-results sees Table 1.
3, compound [5-(furfurylidene imino-)-1,3,4-thiadiazoles-2-yl] sulphur ethyl acetate 2a is as the application of fungistat
With compound [5-(furfurylidene imino-)-1,3,4-thiadiazoles-2-yl] sulphur ethyl acetate 2a is made into 150,100,75, the solution of 50mg/L concentration, adopt growth rate method, study its restraining effect to cucumber fusarium axysporum and botrytis cinerea, make blank assay with distilled water, the solvent of same concentrations (trichloromethane) is made standard control.Controlled temperature is 25 ± 1 ℃ in growth cabinet, and dark illumination was alternately cultivated 3 days, and the right-angled intersection method is measured colony diameter.Calculate this compound restraining effect to cucumber fusarium axysporum and botrytis cinerea under each concentration with following formula: A=(N
0-N)/N
0* 100%, wherein: A is the sample bacteriostatic activity, N
0Be colony diameter in the solvent (trichloromethane), N is a colony diameter in the solution.Experimental result sees Table 2.
Embodiment two
1, compound [5-(o-hydroxy methylene imino-)-1,3,4-thiadiazoles-2-yl] sulphur ethyl acetate 2b's is synthetic
(1) intermediate (5-amino-1,3,4-thiadiazoles-2-yl) sulphur ethyl acetate 1 is synthetic
With embodiment 1.
(2) compound 2b's is synthetic
The compound 1 that in the 50ml round-bottomed flask, adds 5mol, the salicylaldhyde of 5mol, the catalysis of 0.04ml Glacial acetic acid, the 15ml dehydrated alcohol is a solvent, be heated to 75～80 ℃ of stirring and refluxing 2～3h, reaction boils off solvent after finishing, and cooling gets crude product, the dehydrated alcohol recrystallization, get pure product [5-(o-hydroxy methylene imino-)-1,3,4-thiadiazoles-2-yl] sulphur ethyl acetate 2b.Productive rate 79%.
2, compound [5-(o-hydroxy methylene imino-)-1,3,4-thiadiazoles-2-yl] sulphur ethyl acetate 2b is as the application of plant-growth regulator
The same 2a of application method.
3, compound [5-(o-hydroxy methylene imino-)-1,3,4-thiadiazoles-2-yl] sulphur ethyl acetate 2b is as the application of fungistat
The same 2a of application method.
Embodiment three
1, compound [5-(3-methoxyl group-4-hydroxy phenyl methylene radical imino-)-1,3,4-thiadiazoles-2-yl] sulphur ethyl acetate 2c's is synthetic
(1) intermediate (5-amino-1,3,4-thiadiazoles-2-yl) sulphur ethyl acetate 1 is synthetic
With embodiment 1.
(2) compound 1 of adding 5mol in the 50ml round-bottomed flask, the Vanillin of 5mol, the Glacial acetic acid catalysis of 0.04ml, the dehydrated alcohol of 15ml is a solvent, is heated to 75～80 ℃ of stirring and refluxing 2～3h, and reaction boils off solvent after finishing, and cooling gets crude product; The dehydrated alcohol recrystallization gets pure product [5-(3-methoxyl group-4-hydroxy phenyl methylene radical imino-)-1,3,4-thiadiazoles-2-yl] sulphur ethyl acetate 2c.Productive rate 83%.
2, compound [5-(3-methoxyl group-4-hydroxy phenyl methylene radical imino-)-1,3,4-thiadiazoles-2-yl] sulphur ethyl acetate 2c is as the application of plant-growth regulator
The same 2a of application method.
3, compound [5-(3-methoxyl group-4-hydroxy phenyl methylene radical imino-)-1,3,4-thiadiazoles-2-yl] sulphur ethyl acetate 2c is as the application of fungistat
The same 2a of application method.
Embodiment four
1, compound 2d's is synthetic
(1) intermediate (5-amino-1,3,4-thiadiazoles-2-yl) sulphur ethyl acetate 1 is synthetic
With embodiment 1.
(2) compound 2d's is synthetic
The compound 1 that in the 50ml round-bottomed flask, adds 5mol, the terephthalaldehyde of 2.5mol, the catalysis of 0.04ml Glacial acetic acid, the 20ml dehydrated alcohol is a solvent, be heated to 75～80 ℃ of stirring and refluxing 2～3h, reaction boils off solvent after finishing, cooling, get crude product, anhydrous recrystallization gets pure product 1,4-two penylenes-two { [(5-methylene radical imino-)-1,3,4-thiadiazoles-2-yl] the sulphur ethyl acetate } 2d.Productive rate 87%.
2, compound 1, and 4-two penylenes-two { [(5-methylene radical imino-)-1,3,4-thiadiazoles-2-yl] sulphur ethyl acetate } 2d is as the application of plant-growth regulator
The same 2a of application method.
Claims (8)
1. compound [5-(aryl methylene imino-)-1,3,4-thiadiazoles-2-yl] sulphur ethyl acetate, its structure is as follows:
2. compound [5-(aryl methylene imino-)-1 according to claim 1,3,4-thiadiazoles-2-yl] synthetic method of sulphur ethyl acetate is with 2-amino-5-sulfydryl-1,3,4-thiadiazoles and ethyl chloroacetate are raw material, in aqueous phase elder generation synthetic intermediate (5-amino-1,3,4-thiadiazoles-2-yl) sulphur ethyl acetate, make this intermediate and aromatic aldehyde generation condensation again, obtain target product.
3. as compound [5-(aryl methylene imino-)-1 as described in as described in the claim 2,3,4-thiadiazoles-2-yl] synthetic method of sulphur ethyl acetate, it is characterized in that: the synthesis technique of described intermediate (5-amino-1,3,4-thiadiazoles-2-yl) sulphur ethyl acetate is with 2-amino-5-sulfydryl-1 at aqueous phase, 3,4-thiadiazoles and ethyl chloroacetate react 15～30min with 1: 1～1: 1.5 mol ratio under room temperature, suction filtration, washing and get.
4. as compound [5-(aryl methylene imino-)-1 as described in as described in claim 2 or 3,3,4-thiadiazoles-2-yl] synthetic method of sulphur ethyl acetate, it is characterized in that: described intermediate (5-amino-1,3,4-thiadiazoles-2-yl) carry out synthesizing of sulphur ethyl acetate at alkaline aqueous phase.
5. as compound [5-(aryl methylene imino-)-1 as described in as described in the claim 2,3,4-thiadiazoles-2-yl] synthetic method of sulphur ethyl acetate, it is characterized in that: the technology of described intermediate and aromatic aldehyde generation condensation is: be solvent with the dehydrated alcohol, with the Glacial acetic acid is catalyzer, with (5-amino-1,3,4-thiadiazoles-2-yl) sulphur ethyl acetate and aromatic aldehyde are with 1: 1～2: 1 mol ratio, in 75～80 ℃ of following stirring and refluxing 2～3h; Reaction boils off solvent after finishing, and cooling gets pure product [5-(aryl methylene imino-)-1,3,4-thiadiazoles-2-yl] sulphur ethyl acetate with the dehydrated alcohol recrystallization; The amount of described catalyzer Glacial acetic acid is 0.5～1% of an aromatic aldehyde molar weight.
6. as the synthetic method of compound [5-(aryl methylene imino-)-1,3,4-thiadiazoles-2-yl] sulphur ethyl acetate as described in claim 2 or 5, it is characterized in that: described aromatic aldehyde is furfural, salicylaldhyde, Vanillin or terephthalaldehyde.
According to claim 1 compound [5-(aryl methylene imino-)-1,3,4-thiadiazoles-2-yl] sulphur ethyl acetate as the application of plant-growth regulator.
According to claim 1 compound [5-(aryl methylene imino-)-1,3,4-thiadiazoles-2-yl] sulphur ethyl acetate as the application of fungistat.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102358728A (en) * | 2011-09-04 | 2012-02-22 | 聊城大学 | Rubber peptizer and preparation method thereof |
| CN103588727A (en) * | 2013-11-28 | 2014-02-19 | 新乡医学院 | 2-mercapto-1,3,4-thiadiazole derivative, and preparation method and application thereof |
| CN106496157A (en) * | 2016-09-27 | 2017-03-15 | 大连理工大学 | Three classes, 1,3,4 thiadiazoles schiff's base type lube oil additive, preparation method and application |
-
2010
- 2010-01-15 CN CN201010046323A patent/CN101838265A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102358728A (en) * | 2011-09-04 | 2012-02-22 | 聊城大学 | Rubber peptizer and preparation method thereof |
| CN103588727A (en) * | 2013-11-28 | 2014-02-19 | 新乡医学院 | 2-mercapto-1,3,4-thiadiazole derivative, and preparation method and application thereof |
| CN106496157A (en) * | 2016-09-27 | 2017-03-15 | 大连理工大学 | Three classes, 1,3,4 thiadiazoles schiff's base type lube oil additive, preparation method and application |
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