Herbicidally active pyrimidinesalicylic acid compound, its preparation method and its use as herbicide

A pyrimidine salicylic acid and herbicidal activity technology, which is applied in the field of 2,6-bis(oxy) benzoic acid imido ester derivatives, can solve the problems of narrow herbicidal spectrum, poor selectivity, and low herbicidal performance, and achieves a high yield. High rate and good purity

Active Publication Date: 2015-12-30
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] 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 (Bispyribac-sodium) (CN1035292A) and the subsequent development of rice field herbicide pyrimidine Pyriminobac-methyl (JP04368361), pyribenzoxim (EP658549A1, CN1111623) developed by Korea LG Chemicals, pyribenzoxim (CN112793C) developed by Shanghai Institute of Organic Chemistry and other pyrimidine salicylates Herbicides, then the disadvantages of the compounds disclosed in these references are their low herbicidal performance, narrow herbicidal spectrum, poor selectivity, etc.
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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  • Herbicidally active pyrimidinesalicylic acid compound, its preparation method and its use as herbicide
  • Herbicidally active pyrimidinesalicylic acid compound, its preparation method and its use as herbicide
  • Herbicidally active pyrimidinesalicylic acid compound, its preparation method and its use as herbicide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] Embodiment 1: Preparation of 2-trifluoromethylacetophenone oxime

[0046] Add hydroxylamine hydrochloride (8.3g, 120mmol), methanol (150ml), 20% aqueous sodium hydroxide solution (24.0g, 120mmol) and 2-trifluoromethylacetophenone (17.4g, 100mmol) in a 500ml reaction flask, in React under nitrogen protection at 25°C for 3 hours. After the reaction results, distill off methanol under reduced pressure, add water, and filter to obtain 18.1 g of solid 2-trifluoromethylacetophenone oxime, yield 89.1%, melting point: 110.5-112.5 ℃.

Embodiment 2

[0047] Example 2: O-[2,6-bis(4,6-dimethoxypyrimidinyl-2-yloxy)benzoyl](2-trifluoromethyl)acetophenone oxime (HP-001) preparation of

[0048] Add 2,6-bis(4,6-dimethoxy-2-pyrimidinyl-2-oxyl)benzoic acid (21.5g, 50mmol), 2-trifluoromethylacetophenone oxime ( 10.2g, 50.2mmol), DCC (10.7g, 50.6mmol), DMAP (0.60g, 5mmol), 300 ml of dichloromethane, under the protection of nitrogen, react at room temperature for 10 hours, after the reaction results, filter, and the filtrate is reduced Concentrate under reduced pressure to recover dichloromethane, and recrystallize with methanol to obtain white crystals of O-[2,6-bis(4,6-dimethoxypyrimidinyl-2-yloxy)benzoyl](2-trifluoro Methyl) acetophenone oxime 23.6g, yield 76.7%, melting point: 83.3-85.2°C.

[0049] h 1 NMR: (400Hz, CDCl 3),δ(ppm),8.037(t,1H,Ph-CH),7.689(t,1H,Ph-CH),7.578(d,1H,J=7.2Hz,Ph-CH),7.562(d,1H ,J=5.2Hz,Ph-CH),7.503(d,1H,J=4.2Hz,Ph-CH),7.213(d,2H,J=7.2Hz,Ph-CH),5.757(s,2H,PyrimidineCH ),3.797(s,12H,4xCH 3 O),2.297(...

Embodiment 3

[0051] Embodiment 3: the preparation of 3-trifluoromethyl acetophenone oxime

[0052] Add hydroxylamine hydrochloride (6.9g, 100mmol), ethanol (250ml), 20% aqueous sodium hydroxide solution (20.0g, 100mmol) into a 500ml reaction bottle, 3- Trifluoromethylacetophenone (17.4g, 100mmol) was reacted under nitrogen protection at 25°C for 2 hours. After the reaction result, methanol was distilled off under reduced pressure to obtain a solid 3- Trifluoromethyl acetophenone oxime 18.4g, yield 90.6%. Melting point: 79.5~81℃.

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PUM

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Abstract

A pyrimidine salicylate compound with herbicidal activity, its preparation method and its use as a herbicide, the compound is 2,6-bis((4,6-dimethoxypyrimidinyl-2-yl)oxy base) imino benzoate derivatives, which can effectively control weeds such as barnyardgrass, stephenia, bermudagrass, water amaranth, clove Polygonum, knotweed, etc., have a broad-spectrum effect, and are environmentally friendly and low-toxic. human safety.

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 (Bispyribac-sodium) (CN1035292A) and the subsequent development of rice field herbicide pyrimidine Pyriminobac-methyl (JP04368361), pyribenzoxim (EP658549A1, CN1111623) developed by Korea LG Chemicals, pyribenzoxim (CN112793C) developed by Shanghai Institute of Organic Chemistry and other pyrimidine salicylates Herbicides, then the compounds disclosed in these references have the disadvantages of their low herbicidal performance, narrow herb...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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