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1, 2, 4-triazole Schiff base thioether derivative and preparation method and application thereof

A technology of Schiff base sulfides and derivatives, applied in botany equipment and methods, chemicals for biological control, biocides, etc., can solve the problem of increasing the risk of pest resistance, increasing the amount of use, Reduced efficacy of herbicides, etc.

Active Publication Date: 2021-12-03
HEBEI AGRICULTURAL UNIV.
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, due to the long-term and extensive use of the same herbicide or herbicides with the same mechanism of action in recent years, weed resistance has developed rapidly (Perotti V.E., Plant Sci., 2020, 290:110255-110270.), and weed resistance directly It leads to the reduction of herbicide efficacy and the increase of usage, and causes a vicious circle. Therefore, effectively solving weed resistance is an urgent problem to be solved in the creation of new pesticides
[0003]At present, the biological rational design of new pesticide molecules is mainly based on the existing known target enzymes, so as to obtain new compounds with biological activity. Target pesticides will inevitably increase the risk of pest resistance. If pesticides with the same or similar targets are used in rotation, the problem of pest resistance will become more serious (ThomasC.S., Pest Manag.Sci., 2017 ,73:672-677.)

Method used

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  • 1, 2, 4-triazole Schiff base thioether derivative and preparation method and application thereof
  • 1, 2, 4-triazole Schiff base thioether derivative and preparation method and application thereof
  • 1, 2, 4-triazole Schiff base thioether derivative and preparation method and application thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Embodiment 1: the preparation method of compound 2:

[0030] In a 50 ml single-necked round-bottomed flask, add 0.60 mL of 80% hydrazine hydrate solution and 0.0041 mol of aromatic (hetero)cyclic carboxylate 1 successively, and described aromatic (hetero)cyclic carboxylate methyl is selected from: 2-pyridine carboxylate , Methyl thiophene-3-carboxylate, heat the system to reflux, monitor the reaction process with TCL, stop the reaction after about 5 hours of reaction, cool the system to room temperature, add a small amount of absolute ethanol to the reaction solution, and rotary evaporate under reduced pressure The excess hydrazine hydrate was removed, and the residual solid was recrystallized in absolute ethanol to obtain a white solid, which was dried in a vacuum oven, which was aromatic heterocyclic hydrazide 2, with a yield of 85-90%; when R 1 When it is 3-thienyl, the NMR data are as follows:1 HNMR (CD 3 OD,400MHz): δ8.02-8.01(m,1H),7.48-7.47(m,2H). The amount of...

Embodiment 2

[0031] Embodiment 2: the preparation method of compound 3:

[0032] In (0.46g, 0.0082mol) KOH solution in absolute ethanol, add 0.0041mol aromatic (hetero)cyclic hydrazide 2, and add (0.74mL, 0.0123mol) CS 2 Solution, heating up to reflux, TCL monitors the reaction process, after the reaction is over, the solvent is evaporated under reduced pressure, the crude product is the potassium salt of aromatic (hetero) ring-3-oxadiazole mercapto, and this potassium salt is dissolved in 3mL80% hydrazine hydrate Continue the reflux reaction in the solution for about 4 hours, then pour the reaction solution into 200mL ice water to dissolve, use 10% HCl to adjust the pH of the solution to about 5, a yellow precipitate is formed, filter under reduced pressure, and dry overnight in a vacuum oven to obtain 4- Amino-5-mercapto-1,2,4-triazole compound 3, yield 70-82%; when R 1 When it is 3-thienyl, the NMR data are as follows: 1 H NMR (CD 3 Cl, 400MHz): δ8.22 (d, J = 2.0Hz, 1H), 7.44-7.39 (m...

Embodiment 3

[0033] Embodiment 3: the preparation method of compound 4:

[0034] In a dry 50mL round bottom flask, add successively 0.0025mol compound 3, 5mL absolute ethanol solvent, 1.05mL triethylamine, 0.0030mol bromomethyl aryl (hetero) ring derivative, the bromomethyl aryl (hetero) ) ring derivatives are selected from: 1-bromomethyl-2,4-dichlorobenzene, 2-bromomethylpyridine, 4-bromomethyl-3,5-dimethylisoxazole, 3-chloromethyl -1,2,4-Triazolin-5-one, bromomethylcyclopropane, heated to reflux, TLC to monitor the reaction process, after the reaction, the solvent was evaporated under reduced pressure, and the crude product was dissolved in 80mL of dichloromethane , washed with 50mL saturated brine, extracted and separated, dried the organic layer with anhydrous sodium sulfate, filtered with suction, and evaporated the solvent under reduced pressure. The crude product was purified by 200-300 mesh silica gel column chromatography to obtain 1,2,4-triazole amino derivative Matter 4, eluent...

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PUM

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Abstract

The invention provides a 1, 2, 4-triazole Schiff base thioether derivative and a preparation method and application thereof, and relates to the 1, 2, 4-triazole Schiff base thioether derivative which has a chemical structural general formula as shown in 5, in the formula, R1 is selected from 2-pyridyl and 3-thienyl; R< 2 > is selected from 2, 4-dichlorophenyl, 2-pyridyl, 3, 5-dimethyl isoxazolyl, 1, 2, 4-triazoline-5-ketone and cyclopropyl; R3 is selected from 5-chloro-2-fluorophenyl, 4-nitrophenyl, 5-methyl furyl and 2-thienyl; the invention discloses the structural general formula and the synthesis method of the compound, application of the compound as a herbicide, application of the compound in preventing and controlling agricultural, forestry and horticultural weeds in combination with agriculturally acceptable auxiliaries or synergists and commercial herbicides, and a preparation method of the compound.

Description

technical field [0001] The technical scheme of the invention relates to 1,2,4-triazole Schiff base sulfide compounds, in particular to 1,2,4-triazole Schiff base sulfide derivatives. Background technique [0002] The use of herbicides can improve grain yield and quality and play an important role in crop production. However, due to the long-term and extensive use of the same herbicide or herbicides with the same mechanism of action in recent years, weed resistance has developed rapidly (Perotti V.E., Plant Sci., 2020, 290:110255-110270.), and weed resistance directly It leads to the reduction of herbicide efficacy and the increase of usage, and causes a vicious circle. Therefore, effectively solving weed resistance is an urgent problem to be solved in the creation of new pesticides. [0003] At present, the biological rational design of new pesticide molecules is mainly based on the existing known target enzymes, so as to obtain new compounds with biological activity. Rota...

Claims

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Application Information

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IPC IPC(8): C07D409/04C07D409/14C07D413/14C07D401/04C07D405/14C07D401/14A01N43/653A01N43/80A01P13/00
CPCC07D409/04C07D409/14C07D413/14C07D401/04C07D405/14C07D401/14A01N43/653A01N43/80
Inventor 王彦恩张金林陈来
Owner HEBEI AGRICULTURAL UNIV.