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

Benzoxazole-2-oxyphenoxypropionimide type compound as well as synthesis method and application thereof

A technology of oxyphenoxypropionimide and benzoxazole, applied in the field of chemistry, can solve problems such as the safety of rice that have not been reported, and achieve the effect of broad-spectrum herbicide activity

Active Publication Date: 2017-11-24
张建华
View PDF8 Cites 6 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Bioassays have shown that most of these compounds have good herbicidal effects, but no reports on the safety of rice

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
  • Benzoxazole-2-oxyphenoxypropionimide type compound as well as synthesis method and application thereof
  • Benzoxazole-2-oxyphenoxypropionimide type compound as well as synthesis method and application thereof
  • Benzoxazole-2-oxyphenoxypropionimide type compound as well as synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Embodiment 1: (R)-2-[4-(6-chloro-1,3-benzoxazole-2-oxyl)phenoxy]-N,N-dicyanomethylpropionamide (general R in formula (Ⅰ) 1 , R 2 for H, R 3 , R 4 for the synthesis of CN)

[0030] 1) Synthesis of (R)-2-[4-(6-chloro-1,3-benzoxazol-2-oxyl)phenoxypropionic acid:

[0031]

[0032] Add 36.2g (0.1mol) (R)-2-[4-(6-chloro-1,3-benzoxazol-2-oxyl)phenoxy ethyl propionate and 100mL For dioxane (1,4-Dioxane), cool down in an ice-water bath to below 5°C under stirring, slowly add 25g of 12% LiOH aqueous solution dropwise, after the dropwise addition, keep it warm at 20-30°C for 6 hours, and monitor by spotting , the response is complete. Use 20% sulfuric acid aqueous solution to adjust the pH value to 5-7, remove the solvent under reduced pressure, recover the solvent, add 100ml water to the crude product for slurry, and use 20% sulfuric acid aqueous solution to adjust the pH value to 2-3, filter with suction, and wash the filter cake with water for 2 After ~3 times drying,...

Embodiment 2

[0039] Embodiment 2: (R)-2-[4-(6-chloro-1,3-benzoxazole-2-oxyl group) phenoxy group] propionimido ethyl diacetate (general formula (I ) in R 1 , R 2 for H, R 3 , R 4 for COOC 2 h 5 )Synthesis

[0040] 1) Synthesis of (R)-2-[4-(6-chloro-1,3-benzoxazol-2-oxyl)phenoxypropionic acid:

[0041]

[0042] Add 36.2g (0.1mol) (R)-2-[4-(6-chloro-1,3-benzoxazol-2-oxyl)phenoxy ethyl propionate and 100mL Dioxane, cooled to below 0°C in an ice-water bath with stirring, slowly added 25 g of 12% LiOH aqueous solution dropwise, after the dropwise addition, kept warm at 20-25°C for 6 hours, monitored by spotting, and the reaction was complete. Use 20% sulfuric acid aqueous solution to adjust the pH value to 6-7, remove the solvent under reduced pressure, recover the solvent, add 100ml water to the crude product for slurry, and use 20% sulfuric acid aqueous solution to adjust the pH value to 2-3, filter with suction, and wash the filter cake with water for 2 After ~3 times drying, 29.3...

Embodiment 3

[0063] Embodiment 3 50% wettable powder

[0064]

[0065] The components are mixed together and pulverized in a pulverizer until the granules are on par.

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 provides a benzoxazole-2-oxyphenoxypropionimide type compound and application thereof. The benzoxazole-2-oxyphenoxypropionimide type compound is shown as a general formula (I): the formula (I) is shown in the description, wherein R1 and R2 are selected from hydrogen or C1 to C6 alkyl; R3 and R4 are selected from cyano, carboxyl, an ester group and an amide group; R5, R6 and R7 are selected from C1 to C20 alkyl, any mono-substituted or polysubstituted aryl, any mono-substituted or polysubstituted arylmethyl and any mono-substituted or polysubstituted arylethyl. The benzoxazole-2-oxyphenoxypropionimide type compound with a novel structure, provided by the invention, can be used for preventing and controlling weeds for crops and is especially used for preventing and controlling weeds in rice paddy fields.

Description

technical field [0001] The invention belongs to the field of chemistry, and in particular relates to a benzoxazole-2-oxyphenoxypropionimide compound and its synthesis method and application. Background technique [0002] Aryloxyphenoxypropionates (APP) herbicides are a class of widely used acetyl-CoA carboxylase inhibitors, which can efficiently and specifically inhibit the acetyl-CoA carboxylase (ACCase) of grass weeds. Since the 1970s, dipropa-yl, which was developed by Japan's Ishihara Sangyo Co., Ltd. and Hoechst, quickly attracted widespread attention from major pesticide companies and pesticide research institutions around the world, setting off the APP herbicide with dipropa-yl as the lead compound. Agent development upsurge. So far, nearly 20,000 to 30,000 similar APP compounds have been synthesized, nearly 3,000 of which have applied for patents, and the commercialized products include fluoxyfop-pyl, high-efficiency fluoxyfop-op, fluoxyfop, Fluazofop-p-p-p, Quizal...

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): C07D263/58A01N43/76A01P13/00
CPCA01N43/76C07D263/58
Inventor 李剑英吴清来鲁星亮
Owner 张建华