Cis-p-alkyl-1,8-disecondary amine compound, and preparation method and weeding application thereof

A cis-, 1.cis- technology, applied in the fields of botanical equipment and methods, applications, herbicides and algicides, etc., can solve the problems of difficult biodegradation and high toxicity of synthetic pesticides, and achieve high safety and low cost. Wide applicability and mild conditions

Active Publication Date: 2019-08-16
RES INST OF FORESTRY NEW TECH CHINESE ACAD OF FORESTRY +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] In order to solve the defects of high toxicity and difficult biodegradation of synthetic pesticides, this patent discloses a new type of botanical herbicide - cis- Alkane-1,8-disecondary amine compound and its preparation method and application of herbicidal activity

Method used

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  • Cis-p-alkyl-1,8-disecondary amine compound, and preparation method and weeding application thereof
  • Cis-p-alkyl-1,8-disecondary amine compound, and preparation method and weeding application thereof
  • Cis-p-alkyl-1,8-disecondary amine compound, and preparation method and weeding application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] 4.14g (10mmol) cis-pair Alkane-1,8-bis-(4-chlorophenyl) Schiff base (self-made. For the preparation method, refer to the example part of ZL201610942979.3) was added to a three-necked flask containing 20 mL of methanol, and divided into 3 parts under ice-water bath and magnetic stirring. Add 1.513g (40mmol) sodium borohydride each time with an interval of 30min. After the addition, react at room temperature for 2h. After the reaction is complete, add 20mL of water to quench, extract with dichloromethane, collect the organic phase, wash with saturated saline, and anhydrous sulfuric acid Dry over sodium, filter, remove the solvent under reduced pressure, and recrystallize from ethanol to give cis-p The pure product of alkane-1,8-di-(4-chlorobenzyl) secondary amine, the yield is 85%.

[0056] Accurately weigh 1mmol cis-pair Alkane-1,8-bis-(4-chlorophenyl) Schiff base and cis-pair Alkane-1,8-bis-(4-chlorobenzyl)amine was dissolved in 0.25mL DMF, and a drop of Tween 80...

Embodiment 2

[0059] In addition to raw cis-pair Alkane-1,8-disschiff bases are cis-pair Alkane-1,8-bis-(4-fluorophenyl) Schiff base, other operating procedures are the same as in Example 1, the target product cis- Alkane-1,8-bis-(4-fluorobenzyl)amine, yield 98%. cis-pairs of 5mmol / L, 2.5mmol / L, 1.25mmol / L, 0.625mmol / L and 0.3125mmol / L The inhibition rates of alkane-1,8-bis-(4-fluorophenyl) Schiff base solution on barnyardgrass seed stem length were: 32.3%, 20.1%, 23.9%, 2.7% and -13.7%, and the root length The inhibition rates were: 79.7%, 82.9%, 85.7%, 72.8% and 15.7%. cis-pairs of 5mmol / L, 2.5mmol / L, 1.25mmol / L, 0.625mmol / L, 0.3125mmol / L and 0.15625mmol / L The growth inhibition rates of alkane-1,8-bis-(4-fluorobenzyl)amine solution on barnyardgrass seed stems were 100.0%, 85.9%, 75.1%, 58.3%, 10.5% and 7.2%. The growth inhibition rates were: 100.0%, 98.6%, 78.6%, 78.6%, 48.3% and 38.2%.

Embodiment 3

[0061] In addition to raw cis-pair Alkane-1,8-disschiff bases are cis-pair Alkane-1,8-bis-(4-bromophenyl) Schiff base, other operating procedures are the same as in Example 1, the target product cis- The yield of alkane-1,8-bis-(4-bromobenzyl)amine was 96%. cis-pairs of 5mmol / L, 2.5mmol / L, 1.25mmol / L, 0.625mmol / L and 0.3125mmol / L The inhibition rates of alkane-1,8-bis-(4-bromophenyl) Schiff base solution on barnyardgrass seed stem length were 55.9%, 39.3%, 42.3%, 19.6% and 6.5%. The inhibition rates were: 69.4%, 72.6%, 46.8%, 28.5% and -3.2%, respectively. cis-pairs of 5mmol / L, 2.5mmol / L, 1.25mmol / L, 0.625mmol / L, 0.3125mmol / L and 0.15625mmol / L The growth inhibition rates of alkane-1,8-bis-(4-bromobenzyl)amine solution on barnyardgrass seed stems were: 92.3%, 88.2%, 58.5%, 51.7%, 35.4% and 25.2%. The growth inhibition rates were: 100.0%, 97.4%, 89.6%, 83.4%, 57.6% and 30.7%.

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Abstract

The invention discloses a preparation method and a weeding application of a cis-p-alkyl-1,8-disecondary amine compound. The method comprises the following steps: using cis-p-alkyl-1,8-diSchiff base compound as a raw material, adding a educing agent to a polar organic solvent in batches at a temperature of -10-50 DEG C, carrying out a reaction for 1-24 h, quenching the obtained reaction solution with distilled water after the reaction is finished, performing extraction with dichloromethane, drying the obtained extract with anhydrous sodium sulfate, filtering the obtained extract, carrying out reduced pressure distillation to obtain the cis-p-alkyl-1,8-disecondary amine compound, and performing recrystallization or silica gel column chromatography to obtain the pure product. The cis-p-alkyl-1,8-disecondary amine compound is detected by a culture dish seed germination technology, and the weeding activity of the compound is evaluated according to the growth injury symptoms of roots and stems of rice barnyard grass. The method of the invention has the advantages of simple process, mild conditions, high rate, high yield, and wide applicability of the substrate, and the product cis-p-alkyl-1,8-disecondary amine compound has an excellent inhibition effect on the growth of the roots and stems of the rice barnyard grass.

Description

[0001] Technical field: [0002] The present invention relates to cis-pair Alkane-1,8-disecondary amine compounds and their preparation method and application of herbicidal activity, specifically related to a cis- Alkane-1,8-di-Schiff base compounds are used as raw materials, and a reduction reaction occurs with a reducing agent in a polar organic solvent to prepare cis-pair Alkane-1,8-disecondary amine compounds, and use them as herbicidal active ingredients of rice barnyardgrass and the like. Background technique [0003] Since the middle of the 20th century, the use of herbicides has been of great significance to the increase of global food production. However, traditional herbicides are mainly organic synthetic compounds, which are highly toxic, chemically stable, and difficult to biodegrade. Therefore, active development of green , Environmentally friendly high-performance herbicides to replace traditional chemically synthesized herbicides has become a research hotsp...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/29C07C211/27C07C217/58C07C211/49C07C323/32C07D307/56C07D307/52C07D213/38C07D333/20C07D207/335A01N33/04A01N33/10A01N43/40A01N43/36A01N43/08A01N43/10A01P13/00
CPCC07C211/29C07C211/27C07C217/58C07C211/49C07C323/32C07D307/56C07D307/52C07D213/38C07D333/20C07D207/335A01N33/04A01N33/10A01N43/40A01N43/36A01N43/08A01N43/10
Inventor 徐士超赵振东曾小静王婧董欢欢张红梅陈玉湘毕良武
Owner RES INST OF FORESTRY NEW TECH CHINESE ACAD OF FORESTRY
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