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Cyanoacrylate compounds containing fluoro pyridine-methylamino group and their bioactivity

A fluoropicolinyl amino, cyanoacrylate technology, applied in the directions of biocides, plant growth regulators, chemicals used for biological control, etc., can solve the problem of no specific records, no specific records of compounds Herbicidal activity and other issues, to achieve the effects of excellent selectivity, increased selectivity, and safe growth

Inactive Publication Date: 2006-11-29
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0021] Although the above-mentioned documents record that fluorine can be substituted for pyridine, there is no specific description of the cyanoacrylate compounds of the methylamino group of fluorine-substituted pyridine, nor any specific description of the herbicidal activity of these compounds.

Method used

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  • Cyanoacrylate compounds containing fluoro pyridine-methylamino group and their bioactivity
  • Cyanoacrylate compounds containing fluoro pyridine-methylamino group and their bioactivity
  • Cyanoacrylate compounds containing fluoro pyridine-methylamino group and their bioactivity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0039] Embodiment 1: 2-cyano-3, the synthesis of ethyl 3-dimethylthioacrylate

[0040] In a 250ml three-necked flask, add 17.1 grams of finely ground potassium hydroxide powder (0.25mol), and 100ml of dioxane. Cool to 0°C, add 14.1 g of ethyl cyanoacetate (0.125 mol), 9.5 g of carbon disulfide (0.125 mol), and 30 ml of dioxane solution dropwise under vigorous stirring, and add dropwise in about 2 hours. React at room temperature for 2-3 hours, stop the reaction, let it stand, and pour off the upper layer of dioxane to obtain a solid yellow solid. Continue to add 240ml of 95% ethanol and 40ml of water to the reaction flask. Add 34.65 g of dimethyl sulfate (0.275 mol) dropwise at room temperature under stirring, and complete the dropwise addition in 2-4 hours, continue to react at room temperature for about 5 hours, add 1500 ml of water to the system, stir, and precipitate a yellow solid product.

Embodiment 2

[0041] Example 2: Synthesis of 2-cyano-3,3-dimethylthioacrylic acid substituted phenoxyethyl ester

[0042] 0.0634mol potassium hydroxide and 0.0317mol 2-cyanophenoxyethyl ester (1) were added to 20mL of acetonitrile, and 0.0317mol carbon disulfide was added dropwise after 0.5h. After 3 h, 0.0665 mol of dimethyl sulfate was added dropwise under ice-cooling, and the mixture was naturally raised to room temperature, and stirred overnight. Suction filtration, spin dry, recrystallization.

Embodiment 3

[0043] Embodiment 3.2-cyano-3, the synthesis of ethoxyethyl 3-dimethylthioacrylate

[0044] In a 100ml three-necked flask, add 2.74 grams of finely ground potassium hydroxide powder (0.04mol), and 12ml of anhydrous acetonitrile, and after cooling to 5°C, add 2.86 grams of ethoxyethyl cyanoacetate (0.02mol) dropwise, 1.5 The mixed solution of carbon disulfide (0.02mol) and 5ml of anhydrous acetonitrile was dropped in about 30 minutes. Stir at room temperature for 4 hours. Cool to 0°C, add 5.04 grams of dimethyl sulfate (0.04mol) dropwise, complete the dropwise addition in 2 hours, continue to react at room temperature for about 5 hours, add 50ml of water to the system, and separate the generated red oil, namely for the product.

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Abstract

The invention Cyanoacrylate compounds containing fluoro pyridine-methylamino group and their grass-clearing activity, wherein the compound (I) high very high Hill reaction activity and grass-clearing activity, and exhibits fine selectivity for crops, wherein R1 is alkyl, alkoxy, aralkyl, R2 is alkyl or alkyl sulfide.

Description

technical field [0001] The present invention relates to cyanoacrylate compounds of fluoropyridylmethylamino groups and their herbicidal activity. Background technique [0002] Photosynthesis is an important physiological and biochemical process unique to higher green plants and some fungi, but not to animals. Considering toxicity, this provides a solid basis for the selectivity of photosynthetic herbicides. All compounds with inhibitory photosynthetic activity destroy the photoreaction or block electron transfer during photosynthesis. The most studied photosynthesis inhibitors are electron transport inhibitors. [0003] Cyanoacrylates are a special class of PSII electron transport inhibitors. Studies on this type of electron transport inhibitors have shown that slight changes in the structure of these compounds have a significant impact on the Hill reaction inhibitory activity. For example, the introduction of an ether structural group with a relatively electronegative oxy...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D213/61A01N43/40A01P13/00
Inventor 邹小毛杨华铮郁丽敏刘斌胡方中高颖裴江李华斌施欢乐李慧芳
Owner NANKAI UNIV