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Isooxazoline carboxylate compound and application

A technology of isoxazoline carboxylic acid and ester compounds, applied in the field of agricultural herbicides, can solve the problems of satisfactory weed control effect and the like

Active Publication Date: 2020-02-21
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the control effect of these known compounds on weeds is not always completely satisfactory

Method used

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  • Isooxazoline carboxylate compound and application
  • Isooxazoline carboxylate compound and application
  • Isooxazoline carboxylate compound and application

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0081] The preparation of embodiment 1 compound 1

[0082]

[0083] 3-(2-Chloro-4-fluoro-5-(3-methyl-2,6-dioxo-4-trifluoromethyl-3,6-dihydropyrimidin-1(2H)-yl)- Phenyl)-5-methyl-4,5-dihydroisoxazole-5-carboxylic acid (preparation with reference to CN105753853) (0.45g, 0.001mol) was added to a reaction flask with 20ml of dichloromethane, stirred at room temperature Next, dimethylaminoethanol (0.11g, 0.0012mol), DMAP (0.13g, 0.001mol) and EDCI (0.29g, 0.0015mol) were added successively, and the reaction mixture was stirred overnight at room temperature, 100ml of water was added, and washed with ethyl acetate (100ml*2) extraction, the organic phases were combined and dried over anhydrous magnesium sulfate, filtered and desolvated, and column chromatography (ethyl acetate:petroleum ether=1:5) gave 0.19g of oily compound 1.

[0084] 1 H-NMR (300MHz, internal standard TMS, solvent CDCl 3 )δ(ppm): 1.68(s,3H), 2.30(s,6H), 2.62(t,2H), 4.26(t,2H), 3.38(d,1H), 3.60(s,3H), 3.90( d,...

Embodiment 2

[0087] Embodiment 2 Indoor herbicidal activity assay

[0088] The herbicidal activity testing method of compound of the present invention is as follows:

[0089] Quantitative gramineous weeds (barnyardgrass, golden foxtail) and broad-leaved weeds (zinnia, velvetleaf) were sown in paper cups with a diameter of 7 cm and filled with nutrient soil, and covered with 1 cm of soil after sowing. After watering, they were cultivated in the greenhouse according to conventional methods. Gramineae weeds grow to 2-3 leaf stage, and broad-leaved weeds 2-4 leaf stage stem and leaf spray treatment; pre-emergence soil spray treatment is carried out 24 hours after sowing. According to the test design dose, carry out the spray treatment (spray pressure 1.95kg / cm2) on the crawler crop sprayer (Engineer Research Ltd. design and production, UK). 2 , spray volume 500L / hm 2 , crawler speed 1.48km / h). The experiment was repeated 3 times. After treatment, the test materials are placed in the opera...

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PUM

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Abstract

The invention belongs to the field of agricultural herbicides and particularly relates to preparation and application researches on an isooxazoline carboxylate compound and salts thereof. The isooxazoline carboxylate compound and compounds of salts thereof are represented by a general formula (I). The compound represented by the general formula (I) has very good weeding activity, can effectively control weeds such as Echinochloa crusgalli, Setaria viridis, Abutilon theophrasti and zinnia, can obtain a very good weeding effect in case of low dose and can serve as a herbicide agriculturally.

Description

technical field [0001] The invention belongs to the field of agricultural herbicides, in particular to an isoxazoline carboxylate compound and its application. Background technique [0002] The research on uracil compounds as herbicides began in the 1960s and reached its peak in the 1990s. Although there are fewer varieties developed in recent years, there are also patent reports from time to time. For example, Isagro Ricerca disclosed the following general formula in WO2004056785 structure. However, the control effect of these known compounds on weeds is not always completely satisfactory. [0003] [0004] Among them: Q 1 It is a five-membered heterocycle such as thiazole, oxazole, benzothiazole or benzoxazole, etc. Q 2 For F or H. [0005] The company introduced the isoxazoline structure in the early research and development and applied for the patent CN105753853, and disclosed the following general formula compound, wherein R 9 , R 10 respectively selected from...

Claims

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Application Information

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IPC IPC(8): C07D239/54A01N43/54A01P13/00
CPCC07D239/54A01N43/54
Inventor 杨吉春李淼崔东亮吴峤马宏娟刘长令
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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