Furanosyl modified 1,3,4-thiadiazole derivative and preparation method thereof as well as application of derivative as bactericide

A bactericide, phenyl technology, applied to furanosyl-modified 1,3,4-thiadiazole derivatives and their preparation and application as a bactericide, can solve the complex synthesis of glycosyl isothiocyanates , high preparation cost, difficult separation and purification, etc., to achieve the effects of good growth inhibition, cheap raw materials, and simple reaction route

Inactive Publication Date: 2011-08-17
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In 2003, Cao Keguang et al first introduced glycosides into imino-1,3,4-thiadiazole compounds, and designed 8 kinds of 2-aryl-5-(2′,3′,4′,6′-tetra- O-acetyl-β-D-glucopyranosyl)imino-1,3,4-thiadiazoline compound, the antibacterial test shows that the control effect of some compounds on wheat gibberella reaches 85%, but the glycosylation The synthesis of thiocyanate is more complicated and the preparation cost is higher
The synthesis of this series of compounds is not difficult, but due to the existence of spiro rings, the products are prone to produce isomers, which brings difficulties to separation and purification

Method used

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  • Furanosyl modified 1,3,4-thiadiazole derivative and preparation method thereof as well as application of derivative as bactericide
  • Furanosyl modified 1,3,4-thiadiazole derivative and preparation method thereof as well as application of derivative as bactericide
  • Furanosyl modified 1,3,4-thiadiazole derivative and preparation method thereof as well as application of derivative as bactericide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0042] Example 1. Compound CAU-2010-ZJ-A-1 (R=Ac (acetyl) in formula I, R'=4-Cl-2-CF 3 -Phenyl) preparation and structure identification.

[0043]

[0044] In a 100mL round-bottom flask, add 1,2-O-isopropylidene-3-O-acetyl-xylofuranose-5-aldehyde 1.15 g (2, R is acetyl), N-4-Cl-2 -CF 3-Phenylthiosemicarbazide (1.48g, 5.5mmol), dissolved in 30mL of anhydrous dichloromethane, heated to reflux for 6h, directly concentrated after the reaction, the concentrate can be directly entered into the next step reaction, or the concentrate can be quickly Preliminarily separated through a short silica gel column or recrystallized with petroleum ether / ethyl acetate (v / v=6:1) to precipitate a white powder, and the obtained solid was dried and then proceeded to the next step. The obtained crude product was dissolved in an appropriate amount of chloroform, 3.8 g of manganese dioxide was added, and stirred at room temperature for 2 h. After the reaction, the manganese dioxide was removed by ...

Embodiment 2

[0048] Embodiment 2, the preparation of compound CAU-2010-ZJ-A-1 emulsifiable concentrate

[0049] Add compound CAU-2010-ZJ-A-11~10g, emulsifier 5~15g, penetrant 0.1~1g into a 100ml volumetric flask, and then use solvent such as toluene, xylene, etc. to make up the content of 1~10% cream.

[0050] Other emulsifiable concentrates with the general formula of CAU-2010-ZJ compound can be prepared according to the above method.

Embodiment 3

[0051] Embodiment 3, the preparation of compound CAU-2010-ZJ-A-1 wettable powder

[0052] Take compound CAU-2010-ZJ-A-115-50g, surfactant 10-20g, white carbon black 30-75g, mix and pulverize to obtain a wettable powder with a content of 15-50%.

[0053] Wettable powders of other compounds with general formula CAU-2010-ZJ can be prepared according to the above method.

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Abstract

The invention discloses a furanosyl modified 1,3,4-thiadiazole derivative and a preparation method thereof as well as application of the derivative as bactericide. The structural formula of the derivative CAU-2010-ZJ is as shown in a formula I. In the formula, R is acetyl, allyl, propargyl, methyl or ethyl; and R' is isopropyl, naphthaline, phenyl or phenyl having 1-2 substituted groups, wherein the substituted groups are halogen, methyl, methoxy, nitro, trifluoromethyl, or heptafluoro isopropyl. The preparation method comprises the following steps: carrying out a condensation reaction on a compound as shown in a formula II and N-substituted thiosemicarbazide so as to obtain thiosemicarbazone; and then carrying out a MnO2 ring-closing reaction so as to obtain a compound as shown in the formula I. The result of a bactericidal activity assay indicates that the compound CAU-2010-ZJ and a preparation thereof have good growth inhibition effect on sclerotium germs, eggplant early blight germs, gray mold germs, seedbed rhizoctonia solani germs, rice blast germs, asparagus stem blight germs, pythium germs, damping-off fungi, peanut black spot germs, white rot germs, tomato leaf mildew germs and watermelon anthrax. The formula I and formula II are as shown in the specification.

Description

technical field [0001] The present invention relates to a class of furanosyl-modified 1,3,4-thiadiazole derivatives and their preparation method and application as a fungicide. Background technique [0002] The 1,3,4-thiadiazole heterocyclic structure is an important pharmacophore in drug design, and related compounds show good herbicidal, bactericidal, insecticidal and plant growth regulation activities. 2-dodecylidene-5-(substituted imino)-1,3,4-thiadiazoline, 2-hexamethylene-5-(substituted imino)-1 previously studied by the inventors , 3,4-thiadiazoline and macrolide / lactam-1,3,4-thiadiazoline compounds mostly have good bactericidal activity, and some of them have the value of further development. In recent years, structural modification using 1,3,4-thiadiazole structure as the parent to obtain drug varieties with better biological activity has become a research hotspot. While exploring higher biological activity in structural modification, more attention has been paid t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07H9/04C07H1/00A01N43/90A01N43/52A01N43/50A01N37/34A01N25/04A01N25/14A01P3/00
Inventor 张建军宗广辉梁晓梅王道全
Owner CHINA AGRI UNIV
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