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Isoxazoline compound with optical activity and application thereof

An isoxazoline and compound technology, applied in the field of isoxazoline compounds, can solve the problems of no optical isomers, no involving the same or different optical isomers, no involving optical isomers, etc.

Active Publication Date: 2021-04-20
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

But there is no report related to the optical isomers of this class of compounds, nor does it involve whether the herbicidal activity between the optical isomers is the same or different, and it does not involve which optical isomer is more effective as a herbicide active ingredient. Differences are difficult to predict without specific experimental studies

Method used

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  • Isoxazoline compound with optical activity and application thereof
  • Isoxazoline compound with optical activity and application thereof
  • Isoxazoline compound with optical activity and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0097] The preparation of embodiment 1 compound 3

[0098]

[0099] 1) Preparation of ethyl (S)-3-(5-amino-2-chloro-4-fluorophenyl)-5-methyl-4,5-dihydro-5-isoxazolecarboxylate

[0100] Put 25g of Amylose tris (3,5-dimethylphenylcarbamate) silica gel into the chromatographic column, which will contain 1g of 3-(5-amino-2-chloro-4-fluorophenyl)-5-methyl-4,5-dihydro The 5ml dichloromethane solution of ethyl 5-isoxazolecarboxylate (prepared with reference to the method in CN105753853) is adsorbed in the chromatographic column, and is separated by Biotage rapid preparation chromatography, and the corresponding components are collected to obtain optical isomerism (R)-3 -(5-Amino-2-chloro-4-fluorophenyl)-5-methyl-4,5-dihydro-5-isoxazolecarboxylic acid ethyl ester 0.47g (optical purity 99.8%, melting point 105-106 ℃), (S)-3-(5-amino-2-chloro-4-fluorophenyl)-5-methyl-4,5-dihydro-5-isoxazolecarboxylic acid ethyl ester 0.46g (optical Purity 99.4%, melting point 104-105°C).

[0101] ...

Embodiment 2

[0107] Embodiment 2 Indoor herbicidal activity assay

[0108] The herbicidal activity testing method of compound of the present invention is as follows:

[0109] Quantitative gramineous weeds (barnyardgrass, golden foxtail) and broad-leaved weeds (zinnia, velvetleum) seeds were respectively sown in paper cups with a diameter of 7 cm filled with nutrient soil, and covered with soil 1 cm after sowing, pressed, 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 ar...

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PUM

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Abstract

The invention belongs to the field of agricultural herbicides, and particularly relates to an isoxazoline compound with optical activity and application. The isoxazoline compound with optical activity is shown as a general formula (I), a substituent group is shown in the specification, and the compound shown as the general formula (I) has good herbicidal activity, can be used for preemergence and post-emergence weeding, and can also be used for soil treatment. The compound of the general formula (I) can effectively control various broadleaf weeds, gramineous weeds and cyperaceae weeds, and can control various resistant weeds, such as glyphosate-resistant weeds. The compound has good weeding effect at low dosage, has good safety to crops such as corn, wheat, rice, soybean, beet and the like, can be used as a selective herbicide in agriculture, and can also be used as a sterilant herbicide in non-cultivated land leisure land, forest land, orchards, ridges and the like.

Description

technical field [0001] The invention belongs to the field of agricultural herbicides, and in particular relates to an optically active isoxazoline compound and its application. Background technique [0002] CN105753853 discloses isoxazoline compounds having the following general structural formula and herbicidal activity. But there is no report related to the optical isomers of this class of compounds, nor does it involve whether the herbicidal activity between the optical isomers is the same or different, and it does not involve which optical isomer is more effective as a herbicide active ingredient. Differences are difficult to predict without specific experimental studies. [0003] Contents of the invention [0004] The object of the present invention is to provide an optically active isoxazoline compound and its application. [0005] The technology that the present invention adopts for realizing the above object is: [0006] The present invention has the opticall...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D413/10C07D413/14A01N43/80A01P13/00
CPCC07D413/14A01N43/80C07D413/10A01P13/00
Inventor 杨吉春关爱莹崔东亮吴峤马宏娟武恩明刘长令
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD