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Isooxazoline compound and use thereof

A technology of isoxazolines and compounds, applied in application, organic chemistry, biocides, etc., can solve problems such as herbicide resistance

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

[0008] In order to develop novel herbicides to solve the increasingly serious problem of herbicide resistance, the invention provides a kind of isoxazoline compound and its application

Method used

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  • Isooxazoline compound and use thereof
  • Isooxazoline compound and use thereof
  • Isooxazoline compound and use thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0081] The preparation of embodiment 1 compound 18

[0082]

[0083] 1) Preparation of 2-chloro-4-fluoro-5-nitrobenzaldehyde oxime

[0084] Dissolve 42g (0.206mol) of 2-chloro-4-fluoro-5-nitrobenzaldehyde in 200ml of ethanol, drop to 0°C, add dropwise 17.4g (0.25mol) of an aqueous solution of hydroxylamine hydrochloride under stirring, and then raise to room temperature Stir the reaction. After 2 hours, TLC monitored the reaction to be complete. Poured into water, filtered to obtain 38.3g of white solid. The melting point is 103°C.

[0085] 2) Preparation of ethyl 3-(3-(2-chloro-4-fluoro-5-nitrophenyl)-5-methyl-4,5-dihydroisoxazol-5-yl)propionate

[0086] Dissolve 43.7g (0.2mol) of 2-chloro-4-fluoro-5-nitrobenzaldehyde oxime in 150ml of N,N-dimethylformamide, raise the temperature to 30°C, and add 32g ( 0.24mol) NCS to form a light yellow solution, which was kept at 35°C for 1 hour. Cool down to room temperature, add 300ml of dichloromethane, then wash twice with 1N h...

Embodiment 2

[0100] Embodiment 2 Indoor herbicidal activity assay

[0101] The herbicidal activity testing method of compound of the present invention is as follows:

[0102] 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 dosage, carry out the spray treatment (spray pressure 1.95kg / cm2) on the crawler crop sprayer (EngineerResearch Ltd. design and production in England) 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...

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Abstract

The invention belongs to the field of agricultural herbicides and particularly relates to an isooxazoline compound and use thereof. The isooxazoline compound is 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, and in particular relates to an isoxazoline 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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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/10A01N43/80A01P13/00
CPCC07D413/10A01N43/80
Inventor 杨吉春关爱莹崔东亮吴峤颜克成刘长令
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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