Phosphate compound containing 1,2,3-triazole ring as well as preparation method and application thereof

A compound and triazole ring technology, applied in the field of phosphate compounds, can solve the problems of low selectivity and long residual effect period, and achieve the effects of simple reaction route, high plant growth regulation activity and herbicidal activity

Inactive Publication Date: 2015-01-28
CHINA AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The inventor's previous research on 1,3,4-triazole compounds showed that the modification of these structures introduced a novel chlorocycloalkyl group, which can retain and improve the plant growth regulation activity of 1,3,4-triazole At the same time, it can overcome the long residual period and low selectivity of existing commercial varieties to a certain extent. However, it has always been an important task to design and synthesize novel plant growth regulator molecules and to find high-efficiency and high-activity new plant growth regulators. Inventor's focus

Method used

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  • Phosphate compound containing 1,2,3-triazole ring as well as preparation method and application thereof
  • Phosphate compound containing 1,2,3-triazole ring as well as preparation method and application thereof
  • Phosphate compound containing 1,2,3-triazole ring as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Example 1 compound CAU2014-JY-A3, (R 1 is phenyl, R 2 Naphthalene methyl) preparation and structure identification.

[0044]

[0045](1) In a 100ml round bottom flask, add 1.65g (10mmol) of the intermediate, the compound represented by formula (II), 30mL of methanol: water 1:1 solution, 1.06g (20mmol) of ammonium chloride, dissolve and add Sodium nitrogen 1.30g (20mmol), stirred overnight at room temperature. After the reaction is completed, extract three times with dichloromethane-water system, take the organic phase, add anhydrous sodium sulfate, let it stand overnight, and remove the solvent to obtain the crude compound product of the structure shown in formula (III).

[0046] (2) The product obtained in (1) above, that is, the compound represented by formula (Ⅲ), does not need to be purified. It is directly dissolved in 30 mL of methanol:water 1:1 solution, and 0.2 g (1 mmol) of sodium vitamin C and phenylacetylene (11 mmol) are added in sequence. , 0.16 g (1 ...

Embodiment 2

[0061] Embodiment 2, the preparation of compound CAU2014-JY-A3 emulsifiable concentrate (5%)

[0062] Add 35g of compound CAU2014-JY-A, 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 5% emulsifiable concentrate.

[0063] Other emulsifiable concentrates of compounds with the general formula CAU2014-JY can be prepared according to the above method.

Embodiment 3

[0064] Embodiment 3 general formula is the determination of the delaying plant growth activity of the compound of CAU2014-JY

[0065] The test refers to the method of gibberellin bioassay, and the rice leaf sheath spotting method is used. The rice variety is Nipponbare (Oryza sativa L.japonica.cv.Nipponbare, Department of Genetics and Breeding, China Agricultural University).

[0066] Seeds are transferred to a beaker filled with 1% agar after seed soaking and germination cultivation, and cultivated in a light incubator until the top of the first complete leaf stretches out from the first incomplete leaf by about 2mm (at this time, the height of the seedling is about 2mm). 1 cm), use a micro-syringe to drip 1.0 μL of serial concentration medicinal solution between the first incomplete leaf and the first complete leaf (dissolve the compound prepared in Example 1 with a small amount of methanol, and use distilled water containing 1% Tween-80 Diluted to obtain), with paclobutraz...

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Abstract

The invention discloses a phosphate compound containing a 1,2,3-triazole ring as well as a preparation method and an application thereof. The structural formula of the phosphate compound containing the 1,2,3-triazole ring is shown as a formula (I). According to the method for preparing the phosphate compound containing the 1,2,3-triazole ring disclosed by the invention, the raw materials are low in price and readily available, the reaction route is simple, and the phosphate compound containing the 1,2,3-triazole ring is high in herbicidal activity. The measurement result of the herbicidal activity plating method proves that the phosphate compound has strong effects of inhibiting growth of roots and stems of wheat and oilseed rapes. The pot experiment proves that the phosphate compound has a good effect of inhibiting growth of barnyard grass. The phosphate compound containing the 1,2,3-triazole ring has high plant growth regulation activity and high herbicidal activity during low concentration.

Description

technical field [0001] The invention relates to a phosphoric acid ester compound containing 1,2,3-triazole ring, its preparation method and application. Background technique [0002] Heterocyclic ring compounds containing heteroatoms such as N, S, and P are very important chemical structures in the research fields of pesticides, medicines, and veterinary drugs. Acaricides, herbicides, and plant growth regulators are widely used 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 1,3,4-thiadiazole ring structures, such as 2-hexamethylene-5-(substituted imino)-1,3 ,4-thiazoline, 2-dodecamethylene-5-(substituted imino)-1,3,4-thiazoline, macrolide / lactam-1,3,4-thiazoline, furan Most of the glycosyl-modified 1,3,4-thiazoles and 1,3,4-triazole compounds containing chlorocyclopropane have good bacte...

Claims

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Application Information

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IPC IPC(8): C07F9/6518C07F9/6558A01N57/24A01P21/00A01P13/00
Inventor 张建军路慧哲金岩谭伟明梁晓梅段留生王道全
Owner CHINA AGRI UNIV
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