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3-p-*alkene-1-secondary amine type compound and preparing method and weeding application thereof

A compound and secondary amine technology, which is applied in the field of 3-p-*ene-1-secondary amine compounds and their preparation and herbicide applications, can solve the problems of difficult biodegradation and high toxicity of synthetic pesticides, and achieve high safety and low The effect of wide applicability and simple synthesis process

Active Publication Date: 2019-08-09
INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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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, the present invention discloses a new class of botanical herbicides - 3-pair En-1-secondary amine compound and its preparation method and herbicidal application

Method used

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  • 3-p-*alkene-1-secondary amine type compound and preparing method and weeding application thereof
  • 3-p-*alkene-1-secondary amine type compound and preparing method and weeding application thereof
  • 3-p-*alkene-1-secondary amine type compound and preparing method and weeding application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] 5.50g (20mmol) 3-pair En-1-(4-chlorophenyl) Schiff base (self-made. For the preparation method, see: ZL201610947955.7 Examples) was added to a three-necked flask containing 20 mL of methanol, and 1.513 g (40mmol) sodium borohydride, each 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 brine, and dry over anhydrous sodium sulfate. Filter, remove the solvent under reduced pressure, and then purify by silica gel column chromatography to obtain 3-pair En-1-(4-chlorobenzyl)secondary amine, yield 92%.

[0053] Accurately weigh 1mmol 3-pair En-1-(4-chlorophenyl) Schiff base and 3-p Alkene-1-(4-methylthiobenzyl) secondary amines were dissolved in 0.25mL DMF, and a drop of Tween 80 was added dropwise. After fully dissolved, transferred to a 100mL volumetric flask and diluted to the mark with distilled water to o...

Embodiment 2

[0056] In addition to raw materials 3-pair En-1-amine Schiff bases are 3-pair Alkene-1-(4-fluorophenyl) Schiff base, other operation process is the same as embodiment 1, target product 3-pair The yield of en-1-(4-fluorobenzyl) secondary amine was 76.0%. 3-pairs of 10mmol / L, 5mmol / L, 2.5mmol / L, 1.25mmol / L, 0.625mmol / L and 0.3125mmol / L The inhibitory rates of alkenyl-1-(4-fluorophenyl) Schiff base solution to barnyardgrass seed root length are respectively: 88.6%, 87.9%, 86.1%, 65.8%, 41.0% and 26.8%, and the inhibition to stem length The rates were: 97.5%, 94.7%, 74.3%, 56.4%, 44.5% and 40.0%. 3-pairs of 10mmol / L, 5mmol / L, 2.5mmol / L, 1.25mmol / L, 0.625mmol / L and 0.3125mmol / L The inhibitory rates of ene-1-(4-fluorobenzyl) secondary amine solution to barnyardgrass seed root length are respectively: 100.0%, 100.0%, 100.0%, 68.0%, 84.2% and 67.0%, and the inhibitory rates to stem length They are: 100.0%, 100.0%, 100.0%, 85.6%, 65.4% and 56.0%.

Embodiment 3

[0058] 3-pair En-1-amine Schiff base derivatives are 3-pair Alkene-1-(4-methylthiophenyl) Schiff base, other operating procedures are the same as in Example 1, and the target product yield is 73%. 3-pairs of 10mmol / L, 5mmol / L, 2.5mmol / L, 1.25mmol / L, 0.625mmol / L and 0.3125mmol / L The inhibitory rates of alkenyl-1-(4-methylthiobenzyl) secondary amine solution to barnyardgrass seed root length were: 71.8%, 71.4%, 69.5%, 64.9%, 63.9% and 53.1%, and the effect on stem length The inhibition rates were: 86.9%, 67.0%, 49.4%, 45.0%, 35.2% and 21.0%, respectively.

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Abstract

The invention discloses a 3-p-*alkene-1-secondary amine type compound and a preparing method and weeding application thereof. In the method, a 3-p-alkene-1-Schiff base type compound serves as the rawmaterial, in a polarity organic solvent, a reducing agent is put in batches at the temperature from -10 DEG C to 50 DEG C, reaction is conducted for 1-24 hours, reaction liquid is subjected to distilled water quenching, dichloromethane extracting, anhydrous sodium sulfate drying, filtering and depressurized distilling after reaction ends to obtain a crude 3-p-alkene-1-secondary amine type compoundproduct, and the column chromatography on silica gel is conducted to obtain a pure product. The growth injury symptoms of rice barnyard grass roots and stems are measured through a culture dish seedgermination method under the culture of the 3-p-alkene-1-secondary amine type compound with different concentrations, and the weeding activity of the compound is evaluated. The method is simple in process, mild in condition, high in speed, high in yield and wide in substrate application range, and the product 3-p-alkene-1-secondary amine type compound has a quite good restraining effect on the growth of the rice barnyard grass roots and stems.

Description

[0001] Technical field: [0002] The present invention relates to 3-pair En-1-secondary amine compounds and their preparation methods and herbicide applications, specifically related to a 3-pair Alkene-1-Schiff base compounds are used as raw materials, and selective reduction reaction occurs with selective reducing agent in polar organic solvents to prepare 3-pair The herbicidal application of en-1-secondary amine compounds and related products to rice barnyardgrass. Background technique [0003] Weeds are one of the most important factors affecting agricultural production. They not only compete with crops for nutrients, water, sunlight and space, but some are even intermediate hosts of diseases and insect pests, promoting the occurrence of diseases and insect pests and reducing the yield and quality of crops. Since the middle of the 20th century, synthetic pesticides have gradually become one of the most important methods of weed control in agricultural production, playi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/40C07C323/32C07C217/58C07D213/38C07D333/20C07D307/56C07C209/52C07C319/20C07C213/02A01P13/00A01N33/04A01N43/40A01N43/36A01N43/08A01N43/10
CPCC07C211/40C07C323/32C07C217/58C07D213/38C07D333/20C07D307/56A01N33/04A01N43/40A01N43/36A01N43/08A01N43/10C07C2601/16
Inventor 赵振东董欢欢徐士超曾小静陈玉湘毕良武王婧张红梅
Owner INST OF CHEM IND OF FOREST PROD CHINESE ACAD OF FORESTRY
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