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Cyclopropane oxime ester derivatives and preparation method and application thereof

A technology of ester derivatives and cyclopropane oxime, which is applied in the field of cyclopropane oxime ester derivatives and their preparation and application, can solve the problems that do not involve the effect of derivatives, achieve excellent herbicidal activity and simple preparation

Active Publication Date: 2014-01-29
菏泽建数智能科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the above-mentioned bibliographical reports do not involve the effect of the prepared derivatives on weeding

Method used

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  • Cyclopropane oxime ester derivatives and preparation method and application thereof
  • Cyclopropane oxime ester derivatives and preparation method and application thereof
  • Cyclopropane oxime ester derivatives and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment 1, the preparation of compound 3a

[0034] Add 3.5mmol of o-tolualdehyde oxime, 0.43g (4.2mmol) of triethylamine, 10mL of THF into a 50mL four-necked round bottom bottle, cool to below 5°C, and slowly add 0.68g (4.2mmol) of ) of cyclopropylformyl chloride in 5mL THF solution, after the addition was complete, stir at room temperature until the aldoxime reaction was complete (monitored by TLC). After the reaction is complete, wash with 10% aqueous sodium bicarbonate, wash with water until neutral, separate the organic phase, anhydrous MgSO 4 Drying, filtration, and solvent removal gave the crude product, which was recrystallized from petroleum ether to obtain compound 3a. The yield, physical and chemical constants and elemental analysis results of compound 3a are shown in Table 1, MS and 1 See Table 2 for H NMR data.

Embodiment 2

[0035] The preparation of embodiment 2 compound 3b

[0036] Add 3.5mmol p-tolualdehyde oxime, 0.43g (4.2mmol) triethylamine, 10mL THF into a 50mL four-neck round bottom bottle, cool to below 5°C, slowly add dropwise 0.68g (4.2mmol) ) of cyclopropylformyl chloride in 5mL THF solution, after the addition was complete, stir at room temperature until the aldoxime reaction was complete (monitored by TLC). After the reaction is complete, wash with 10% aqueous sodium bicarbonate, wash with water until neutral, separate the organic phase, anhydrous MgSO 4 Drying, filtration, and solvent removal gave a crude product, which was recrystallized from petroleum ether to obtain compound 3b. The yield, physical and chemical constants and elemental analysis results of compound 3b are shown in Table 1, MS and 1 See Table 2 for H NMR data.

Embodiment 3

[0037] The preparation of embodiment 3 compound 3c

[0038] Add 3.5mmol of p-bromobenzaldehyde oxime, 0.43g (4.2mmol) of triethylamine, 10mL of THF into a 50mL four-neck round bottom bottle, cool to below 5°C, and slowly add 0.68g (4.2mmol) of Cyclopropylformyl chloride in 5 mL THF solution, after the addition was completed, stirred at room temperature until the aldoxime reaction was complete (monitored by TLC). After the reaction is complete, wash with 10% aqueous sodium bicarbonate solution, wash with water until neutral, separate the organic phase, anhydrous MgSO 4 Drying, filtration, and solvent removal gave a crude product, which was recrystallized from petroleum ether to obtain compound 3c. The yield, physical and chemical constants and elemental analysis results of compound 3c are shown in Table 1, MS and 1 H NMR data in Table 2

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Abstract

The invention discloses cyclopropane oxime ester derivatives and a preparation method and application thereof. The cyclopropane oxime ester derivatives have a structural as a formula (I), wherein R1 refers to phenyl, furyl or substituted phenyl; R2 refers to hydrogen or cyan; a benzene ring of the substituted phenyl is subjected to monosubstitution or multi-substitution, and the substituent groups are respectively independently selected from C1-C10 alkyl, C1-C10 alkoxy, halogen and nitryl; and when the R2 refers to hydrogen, R1 does not refer to m-nitrophenyl. The cyclopropane oxime ester derivatives are easy to prepare, have excellent weeding activity and can be used as herbicides.

Description

(1) Technical field [0001] The invention relates to a cyclopropane oxime ester derivative and its preparation method and application. (2) Background technology [0002] Since the 1960s, pesticides containing oxime structures have frequently appeared in insecticides and acaricides, fungicides, herbicides, and plant growth regulators. Among them, oxime ester compounds have good biological activities such as insecticidal, acaricidal, bactericidal, weeding, anti-plant virus, and synergistic effects. Many varieties have the advantages of high efficiency, low toxicity, and low residue. Oxime ester compounds are used as a kind of Pesticide active compounds have been widely researched and applied. In the 1960s, the developed insecticides were mainly oxime ester pesticides, such as carbamate oxime esters, oxime phosphates, and oxime esters with organophosphorus and carbamate. The ester double structure insecticide phosfoam (U47319). Since the 1980s, oxime pesticides have developed ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C251/66C07C249/12C07C255/64C07C253/30C07D307/52A01N53/00A01P13/00
Inventor 刘幸海李正名张传玉王宝雷谭成侠翁建全
Owner 菏泽建数智能科技有限公司
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