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Aryl triazole compound containing chlorinated cyclopropane and preparation method and application thereof

A technology for substituting cyclopropanyl and aryl triazoles, which is applied in the field of aryl triazole compounds, can solve the problems of long residual effect and low selectivity, and achieve the effect of cheap raw materials, wide application value and good growth inhibition effect

Inactive Publication Date: 2014-03-26
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The research group’s previous research on the fungicidal activity of 1,3,4-thiadiazole derivatives modified with fifteen-membered rings, twelve-membered rings and six-membered rings showed that the size of the ring has a great influence on the activity of these compounds. The bactericidal activity of the 12-membered ring replaced by the 6-membered ring is improved. At the same time, the bactericidal activity of prothioconazole, cyproconazole and other fungicides containing three-membered ring modifications is better than that of tebuconazole without the three-membered ring. However, triazole compounds have certain plant growth regulating activity and bactericidal activity. The commercial products contain triazole ring in the structure of uniconazole and paclobutrazol, but in practical application, the existing commercial varieties have a certain long residual effect period, Insufficiencies such as low selectivity, looking for efficient and highly active new plant growth regulators are the focus of people's attention

Method used

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  • Aryl triazole compound containing chlorinated cyclopropane and preparation method and application thereof
  • Aryl triazole compound containing chlorinated cyclopropane and preparation method and application thereof
  • Aryl triazole compound containing chlorinated cyclopropane and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Example 1. Preparation and structure identification of compound CAUZJ-A-02 (X=CO; R is p-bromophenyl).

[0048] The reaction equation of the present embodiment is as follows:

[0049]

[0050] (1) Add 1-acetyl-1-chlorocyclopropane (Formula II, 10g, 0.084mol) into a 100ml round bottom flask, dissolve in 25ml of anhydrous dichloromethane, and slowly add sulfonyl chloride dropwise under ice-bath conditions (8.45ml, 0.101mol), continue to react for 8h after dripping, add water to quench, extract with dichloromethane, evaporate dichloromethane after drying, and obtain 8g of light green clear liquid with pungent smell, yield 62%. That is formula III.

[0051] (2) Take the product 1-chloroacetyl-1-chlorocyclopropane obtained in (1), i.e. formula III (5g, 0.033mol), and put it in a 250ml round bottom flask, dissolve it in 100ml of ethyl acetate, add 1, 2,4-Triazole (2.3g, 0.033mol), anhydrous potassium carbonate (5.98g, 0.043mol), tetrabutylammonium iodide (0.36g, 0.98mmol...

Embodiment 2

[0056] Example 2. Preparation and structure identification of compound CAUZJ-A-13 (X=CHOH; R is p-bromophenyl).

[0057] The reaction equation prepared in this embodiment is as follows:

[0058]

[0059] Take 0.5g (1.4mmoL) of CAUZJ-A-02 into a 50ml round bottom flask, add 25ml of methanol to dissolve, add 0.1g (2.6mmoL) of sodium borohydride under ice bath conditions, and react for 3 hours. After the reaction, add water, extract with ethyl acetate, dry and recrystallize to obtain 0.35g CAUZJ-A-13, the yield is 70%, m.p.96℃

[0060] Structural Confirmation Data:

[0061] 1 H NMR (300MHz, CDCl 3 )δ0.426-0.507(m,1H,CH 2 ),0.708-0.789(m,1H,CH 2 ),1.005-1.085(m,1H,CH 2 ),1.102-1.255(m,1H,CH 2 ),3.271-3.298(d,2H,CH 2 Ar),3.955-3.970(d,1H,CHOH),4.832-4.856(m,1H,NCH),6.834-6.861(m,4H,ArH),7.788(s,1H,Triazole-H),7.967(s , 1H, Triazole-H).

[0062] Other series of compounds with the general formula CAUZJ-A-13-19 were prepared according to the above method. Their compound ...

Embodiment 3

[0068] Embodiment 3, the preparation of compound CAUZJ-A-02 emulsifiable concentrate (5%)

[0069] Add 5g of compound CAUZJ-A-04, 15g of Nongru 0203B, and 10.6g of penetrant JFC-10.6g into a 100mL volumetric flask, and then dilute to the volume with solvent toluene to obtain an emulsifiable concentrate with a content of 5%.

[0070] Other emulsifiable concentrates of compounds with the general formula CAUZJ-A can be prepared according to the above method.

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Abstract

The invention discloses an aryl triazole compound containing chlorinated cyclopropane and a preparation method and application thereof. The structural formula of the aryl triazole compound containing chlorinated cyclopropane is shown in formula I, wherein X represents C=O or CHOH, and R represents a substituent phenyl group; the substituent in the substituent phenyl group is any one of the following groups: halogen, methyl group, methoxyl group, nitro group, trifluoromethyl group, amino group, and acetyl amino group. The preparation method, provided by the invention, adopts cheap raw materials, and takes a simple reaction route; the synthesized compound has both plant growth regulating activity and bactericidal activity, thereby having a wider application range; in application experiments of the aryl triazole compound containing chlorinated cyclopropane, the plant growth regulating activity shows that the synthesized compound manifests excellent plant growth regulating activity; in application experiments of the aryl triazole compound containing chlorinated cyclopropane, the bactericidal activity test result shows that the compound has excellent growth inhibition effect on sclerotinia sclerotiorum, tomato fungus phytophthora, botrytis cinerea, rhizoctonia solani seedbed, blast fungus, asparagus stem blight, fusarium graminearum, pythium germs, and the like.

Description

technical field [0001] The invention relates to an aryl triazole compound containing chlorinated cyclopropane, a preparation method and application thereof. Background technique [0002] Five-membered ring compounds containing heteroatoms such as N and S are chemical structures that have attracted wide attention in the research fields of medicine, pesticides and veterinary drugs. Due to their different fine structures, these compounds often have unique insecticidal, acaricidal, bactericidal, Activities such as herbicide and plant growth regulation can be used as insecticide, acaricide, fungicide, herbicide, plant growth regulator and anthelmintic in agriculture. Many pesticides of this type are currently commercialized and have good biological activity. The inventor obtained a series of active structures in the synthesis and biological activity research of compounds containing five-membered heterocyclic structures of 1,3,4-thiadiazole, such as 2-dodecamethylene-5-(substitut...

Claims

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Application Information

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IPC IPC(8): C07D249/08A01N43/653A01P21/00A01P3/00
CPCA01N43/653C07D249/08
Inventor 张建军许一仁谭伟明梁晓梅段留生王道全
Owner CHINA AGRI UNIV
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