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2-pyrimidinyloxy-n-aryl azabenzylamine compound, its preparation method, herbicide and application

A technology of aryl azabenzylamine and pyrimidinyloxy, which is applied in the field of 2-pyrimidinyloxy-N-arylazabenzylamine compounds, and can solve the problems of poor selectivity and low universality

Inactive Publication Date: 2018-07-13
SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The technical problem to be solved by the present invention is that, in order to overcome the poor selectivity and low universality of the existing pyrimidinyloxybenzyl substituted arylamine derivative herbicides to soybean and other crops, in order to ensure better herbicidal activity At the same time, it only has the defect of better safety for crop rape, and provides a kind of 2-pyrimidinyloxy-N-aryl azabenzylamine compound, its preparation method, herbicide and application

Method used

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  • 2-pyrimidinyloxy-n-aryl azabenzylamine compound, its preparation method, herbicide and application
  • 2-pyrimidinyloxy-n-aryl azabenzylamine compound, its preparation method, herbicide and application
  • 2-pyrimidinyloxy-n-aryl azabenzylamine compound, its preparation method, herbicide and application

Examples

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preparation example Construction

[0081] Examples of preparation methods of compounds 2-42 of the present invention Referring to Example 1, select corresponding reaction raw materials according to different products.

[0082] In Examples 43-47, all "%" refer to percentage by weight, "g a.i. / hm 2 "All refer to grams of active substance / ha.

Embodiment 1

[0083] Synthesis of embodiment 1 compound (1)

[0084]

[0085] 1) 2-[(phenylimino)methyl]-1-azabenzene-3-ol (g)

[0086] At 10-15°C, add aniline (3.97g, 42.64mmol) into a solution of 3-hydroxy-2-pyridinecarbaldehyde (f, 5.00g, 40.61mmol) in anhydrous methanol (80mL), stir for 1h to precipitate a yellow solid, The mixed system was left to stand for 5 h, filtered, and the yellow solid was washed with a small amount of anhydrous methanol (5 mL / time) precooled to below 5°C. The yellow solid was dried in vacuo to obtain the target compound 2-[(phenylimino)methyl]-1-azabenzene-3-ol (g, 7.36g, 92%).

[0087] 2) 2-[(phenylamino)methyl]-1-azabenzene-3-ol (h)

[0088] At 0-5°C, sodium borohydride (4.07g, 107.45mmol) was added in batches to 2-[(phenylimino)methyl]-1-azaphenol (g, 7.10g, 35.82mmol) and no In a suspension of water and methanol (150 mL), stirring was continued for 30 min. After the reaction, add saturated ammonium chloride solution (70mL) to the reaction system, sti...

Embodiment 2

[0092] n-Propyl N-[2-(4,6-dimethoxypyrimidinyloxy)-6-azabenzylamino]benzoate (2): white solid, mp: 110.5–111.6℃.ESI-MS(m / z):425[M+H] + ,447[M+Na] + . 1 H NMR (300MHz, DMSO) δ8.53–8.33 (m, 1H), 7.70 (d, J = 8.0Hz, 1H), 7.59 (d, J = 8.2Hz, 2H), 7.41 (s, 1H), 6.58 (d, J=8.2Hz, 2H), 6.00(s, 1H), 4.37(d, J=4.6Hz, 2H), 4.09(t, J=6.0Hz, 2H), 3.71(s, 6H), 1.64 (dd,J=13.8,6.8Hz,2H),0.92(t,J=7.1Hz,3H).

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Abstract

The invention discloses a 2-pyrimidinyloxy-N-arylazabenzylamine compound, a preparation method, a herbicide and application thereof. The preparation method of the compound comprises: in a polar non-proton solvent, and under the action of an acid-binding agent, reacting compound C with 2, 6-dimethoxy-4-methylsulfonyl pyrimidine. The invention also provides application of the compound in herbicides. The compound provided by the invention has excellent weeding effect on barnyard grass, Eclipta prostrata, amaranthus retroflexus, brassica juncea and purslane, and has high safety to crop soybean. (reaction formula).

Description

technical field [0001] The invention relates to a 2-pyrimidinyloxy-N-aryl azabenzylamine compound, its preparation method, herbicide and application. Background technique [0002] Lv Long and others reported a class of pyrimidinyloxybenzyl substituted arylamine derivatives, preparation methods and their application as agrochemical herbicides (ZL 00130735.5, US 6800590, KR 0511489, MX 234202, EP 1327629, JP4052942, CA 2425984, PL 216218), they have good herbicidal activity. Based on this, the rapeseed herbicides Propisofen and Mesofen were successfully developed, but Propisofen and Mesofen have no selectivity for other crops, especially for soybeans, which are phytotoxic and safe Poor resistance, therefore, can not be used as soybean field herbicide. Contents of the invention [0003] The technical problem to be solved by the present invention is that, in order to overcome the poor selectivity and low universality of the existing pyrimidinyloxybenzyl substituted arylamine...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/12C07D401/14C07D417/14A01N43/54A01N43/78A01P13/00
CPCA01N43/54A01N43/78C07D401/12C07D401/14C07D417/14
Inventor 吕龙杨征敏唐庆红付群梅
Owner SHANGHAI INST OF ORGANIC CHEM CHINESE ACAD OF SCI