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Novel herbicidal active pyridine salicylic acid compound, prepare method thereof, and purpose of being herbicidal

A pyrimidine salicylic acid, herbicidal activity technology, applied in the field of 2,6-bis(oxy) benzoic acid imido ester derivatives, can solve the problems of narrow herbicidal spectrum, low herbicidal performance, poor selectivity, etc. The effect of good purity, environmental friendliness and high yield

Active Publication Date: 2015-01-21
常州瑞平化工有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] In the late 1980s, the pyrimidine salicylic acid herbicides were first discovered and developed by Japan Combination Chemicals, the first commercial herbicide Bispyribac -sodium) (CN 1035292A) and the subsequently developed paddy field herbicide Pyriminobac-methyl (JP 04368361), pyribenzoxim (EP 658549 A1, CN 1111623) developed by Korea LG Chemical Company, The pyrimidine salicylic acid herbicides such as Propoxyfen (CN112793C) developed by Shanghai Institute of Organic Chemistry, etc., and the disadvantages of the compounds disclosed in these references are their low herbicidal performance, narrow herbicidal spectrum, poor selectivity, etc. In some areas, the use of the above herbicides for many years has produced obvious resistance
However, there is no report about a kind of pyrimidine salicylic acid herbicide with high safety, broad-spectrum effect, environmental friendliness, low toxicity, safety to humans, and wide application prospects in the field of pesticides.

Method used

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  • Novel herbicidal active pyridine salicylic acid compound, prepare method thereof, and purpose of being herbicidal
  • Novel herbicidal active pyridine salicylic acid compound, prepare method thereof, and purpose of being herbicidal
  • Novel herbicidal active pyridine salicylic acid compound, prepare method thereof, and purpose of being herbicidal

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] Embodiment 1: Preparation of 2-trifluoromethylacetophenone oxime

[0045] Add hydroxylamine hydrochloride (8.3 g, 120 mmol), methanol (150 ml), 20% aqueous sodium hydroxide solution (24.0 g, 120 mmol), 2-trifluoromethylacetophenone (17.4 g, 100 mmol), reacted under nitrogen protection at 25°C for 3 hours, after the reaction results, distilled off methanol under reduced pressure, added water, filtered to obtain 18.1 g of solid 2-trifluoromethyl acetophenone oxime, yield 89.1%, Melting point: 110.5-112.5°C.

Embodiment 2

[0046] Example 2: O-[2,6-bis(4,6-dimethoxypyrimidinyl-2-yloxy)benzoyl](2-trifluoromethyl)acetophenone oxime (HP-001) preparation of

[0047] Add 2,6-bis(4,6-dimethoxy-2-pyrimidinyl-2-oxyl)benzoic acid (21.5 g, 50 mmol), oxalyl chloride (12.7 g, 100.0 mmol) into a 500 ml reaction flask , 0.5 milliliters of N, N-dimethylformamide, 250 milliliters of dichloromethane, heated and refluxed for 8 hours, after the reaction was completed, the excessive oxalyl chloride and the organic solvent dichloromethane were evaporated under vacuum and reduced pressure, cooled to room temperature, and dichloromethane was added Chloromethane 300 ml, 2-trifluoromethylacetophenone oxime (10.2 g, 50.2 mmol), DMAP (0.60 g, 5 mmol), under the protection of nitrogen, react at room temperature for 10 hours, after the reaction results, the reaction solution is Concentrate under reduced pressure to recover dichloromethane, and recrystallize with methanol to obtain white crystals of O-[2,6-bis(4,6-dimethox...

Embodiment 3

[0050] Embodiment 3: the preparation of 3-trifluoromethyl acetophenone oxime

[0051] Add hydroxylamine hydrochloride (6.9 g, 100 mmol), ethanol (250 ml), 20% aqueous sodium hydroxide solution (20.0 g, 100 mmol) and 3- Trifluoromethylacetophenone (17.4 g, 100 mmol) was reacted under nitrogen protection at 25°C for 2 hours. After the reaction was completed, methanol was distilled off under reduced pressure to obtain a solid 3- Trifluoromethyl acetophenone oxime 18.5g, yield 90.6%. Melting point: 79.6~81℃.

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Abstract

A novel herbicidal active pyridine salicylic acid compound, a prepare method thereof, and a purpose of being herbicidal are provided. The compound refers to 2,6-bi ((4,6-bi-dimethyl oxygen primidyl-2-base)oxygen base) benzoic acid sub-urethano ramification, can effectively remove weeds like barnyard grass, moleplant seed, monochoria vaginalis, ammannia baccifera,seedbox, and rotala indica; the compound has broad spectrum effect, and is friendly to environment, low toxic, and safe with human people.

Description

technical field [0001] The present invention relates to a novel herbicidally active pyrimidine salicylic acid compound, more specifically, the present invention relates to a novel herbicidal 2,6-bis((4,6-dimethoxypyrimidinyl-2-yl) Oxygen) benzoic acid imidate derivatives, a process for their preparation and their use as herbicides. Background technique [0002] At the end of the 1980s, pyrimidine salicylic acid herbicides were first discovered and developed by Japan Combination Chemicals, the first commercial herbicide Bispyribac-sodium (CN 1035292A) and the subsequent development of herbicides for rice fields Pyriminobac-methyl (JP 04368361), pyribenzoxim (EP 658549 A1, CN 1111623) developed by South Korean LG Chemical Company, propyl acetofen (CN112793C) developed by Shanghai Institute of Organic Chemistry, etc. Pyrimidine salicylic acid herbicides, and the disadvantages of the compounds disclosed in these references are their low herbicidal performance, narrow herbicidal...

Claims

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Application Information

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IPC IPC(8): C07D239/60A01P13/00
CPCA01N43/54C07D239/60
Inventor 徐德锋
Owner 常州瑞平化工有限公司
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