Unlock instant, AI-driven research and patent intelligence for your innovation.

Discovery and application of novel structure and novel function of sulfonyl urea herbicides with controllable soil degradation speed

A technology of sulfonylureas and C1-C6, which is applied in the field of preparation of sulfonylurea derivatives, can solve problems such as the impact of compound degradation behavior, achieve the effect of reducing growth hazards at seedling stage and improving safety

Pending Publication Date: 2021-01-19
NANKAI UNIV
View PDF0 Cites 1 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Then, it was noticed that there were reports that the 5-position substituted iodosulfuron-methyl-sodium (Iodosulfuron-methyl-sodium) and the new structure of foramsulfuron (Foramsulfuron) and other structures degraded faster in soil, and analyzed the above-mentioned several commercialized sulfuron Based on the structure of ureide herbicides, we boldly speculate that the introduction of the 5-position substituent group on the aromatic ring may have a general impact on the degradation behavior of the compound

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Discovery and application of novel structure and novel function of sulfonyl urea herbicides with controllable soil degradation speed
  • Discovery and application of novel structure and novel function of sulfonyl urea herbicides with controllable soil degradation speed
  • Discovery and application of novel structure and novel function of sulfonyl urea herbicides with controllable soil degradation speed

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Synthesis of ethyl 2-chloro-5-amino-benzenesulfonamide carboxylate

[0042]

[0043] In a 100 mL single-necked round bottom flask, 2-chloro-5-amino-benzenesulfonamide (2.06 g, 0.01 mol), potassium carbonate (2.76 g, 0.02 mol) were dissolved in 30 mL of acetone, and then ethyl chloroformate ( 1.30g, 0.012mol), heated to reflux overnight, concentrated under reduced pressure to remove the solvent acetone, the residue was dissolved in a mixed solvent of ether and water (50mL, v / v=1:1), the ether layer was removed by separation, and the water layer was washed with hydrochloric acid Adjust the pH to about 3, and a solid precipitates out, which is filtered by suction and dried to obtain a white solid, which is directly used in the next reaction.

Embodiment 2

[0045] Synthesis of 1-(2-chloro-5-amino-phenylsulfonyl)-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea

[0046]

[0047] In a 100mL single-necked round bottom flask, ethyl 2-chloro-5-amino-benzenesulfonyl formate (2.78g, 0.01mol), 4-methyl-6-methoxy-2-amino-1,3 , 5-triazine (0.14g, 0.01mol) was dissolved in 40mL of toluene and heated to reflux overnight. After the reaction was completed, it was cooled to room temperature, the reaction solution was desolvated, and the residue was purified by column chromatography to obtain the target compound.

[0048] The derivatives 1-2212 prepared by using different raw materials according to the preparation methods of Examples 1-2 are listed in Table 1, some derivatives 1 H NMR (Bruker AV400 spectrometer using tetramethylsilaneas the internal standard), high-resolution mass spectrometry (HRMS), and ultraviolet maximum absorbance (UV) data are listed in Table 2

[0049] Table 1 Structures of Target Compounds I and II

[0050]

[0051...

Embodiment 3

[0119] Plate method: take rape (Brassicanapus) as the test object, pour 2mL of the prepared sample solution into a petri dish (diameter 6cm) covered with filter paper, add 15 rape seeds soaked in distilled water for 4 hours in advance, and then Put the petri dish into a greenhouse (25±2°C) and incubate in the dark for 65 hours, observe the germination of rapeseed, measure the corresponding embryo length, and compare it with the blank control to obtain the corresponding inhibition rate.

[0120] The results of some compounds obtained by plate method to rape inhibition rate are shown in table 3:

[0121]The rape inhibition rate of table 3 part target compound I and II

[0122]

[0123] From the rapeseed inhibition results shown in Table 3, the tested compound is basically in the concentration range of 0.1 μg / ml to 10 μg / ml, which is equivalent to the herbicidal activity of the reference drug chlorsulfuron (No.2212); The herbicidal activity of the structure is slightly lower ...

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention relates to discovery and application of a novel structure and a novel function of sulfonyl urea herbicides with a controllable soil degradation speed. The structures are shown as generalformulas I and II, and definitions of substituent groups in the formulas are shown in the specification. The invention aims to provide a novel sulfonyl urea herbicide which has ultrahigh herbicidal activity, is safe to next-stubble crops, has a relatively high degradation speed and is suitable for a cultivation mode of 2-3 stubble crops in Chinese farmlands every year. Different substituent groups are introduced into the site 5 of a sulfonyl urea benzene ring, a preparation method of a benzene ring site 5 substituted derivative is developed, a new structure with a high degradation rate is found, and a four-factor linkage relationship of a chemical structure / biological activity / environmental degradation / next-stubble crop safety of the chlorsulfuron derivative is proposed for the first timeto replace a traditional structure / activity relationship. The relationship among the four factors is simulated and calculated through computer software, and an optimal result is screened, so that thepurpose of creating the novel sulfonyl urea herbicide with controllable degradation speed according to the requirements of different crops is achieved.

Description

technical field [0001] The present invention relates to the synthesis technology and soil degradation method of agricultural chemical herbicides, in particular to the preparation of sulfonylurea derivatives substituted at the 5-position of the benzene ring, soil degradation research, herbicidal activity research, safety to next crops, and computer software Research and application of the linkage relationship among compound structure, herbicidal activity, soil degradation rate and crop safety. Background technique [0002] In the 1970s, G. Levitt of DuPont Company in the United States first discovered sulfonylurea herbicides. In 1981, the first commercialized variety of chlorsulfuron came out, opening up an era of super-efficient herbicide development. This type of herbicide Because of its ultra-high efficiency, basic non-toxicity to mammals, broad spectrum, high selectivity and other characteristics, it has been widely used. At present, there are dozens of commercial varieti...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07D251/22C07D251/16C07D251/18C07D251/46C07D251/52C07D239/42C07D239/47C07D239/48C07D239/52A01N43/54A01N43/66A01N43/68A01N43/70A01P13/00
CPCA01N43/54A01N43/66A01N43/68A01N43/70C07D239/42C07D239/47C07D239/48C07D239/52C07D251/16C07D251/18C07D251/22C07D251/46C07D251/52
Inventor 李正名武磊孟凡飞周沙华学文周莎李永红马翼
Owner NANKAI UNIV
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com