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Heterocyclic asymmetric aromatic dithioether compound and synthesis method and application thereof

An asymmetric and disulfide technology, applied in the field of asymmetric aromatic disulfide compounds and herbicide preparation, to achieve good herbicidal activity and obvious inhibitory effect

Inactive Publication Date: 2012-10-03
NANKAI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, with the widespread use of these existing types of herbicides, the problem of weed resistance to the four known AHAS inhibitors cannot be ignored.

Method used

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  • Heterocyclic asymmetric aromatic dithioether compound and synthesis method and application thereof
  • Heterocyclic asymmetric aromatic dithioether compound and synthesis method and application thereof
  • Heterocyclic asymmetric aromatic dithioether compound and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Embodiment 1: the preparation of benzenesulfenyl chloride

[0031]

[0032] Dissolve 1.1g (10mmol) of thiophenol in 20mL of dichloromethane, add 1.35g (10mmol) of sulfonyl chloride dropwise at the temperature of an ice-water bath, and stir for 1h. The solvent was removed in vacuo to obtain 1.36 g of red benzenesulfenyl chloride with a yield of 95%, which was directly used in the next reaction.

[0033] Similarly, p-toluenesulfenyl chloride, p-methoxybenzenesulfenyl chloride, p-bromobenzenesulfenyl chloride, p-chlorobenzenesulfenyl chloride, o-fluorobenzenesulfenyl chloride, o-toluenesulfenyl chloride, β-naphthenesulfenyl chloride.

Embodiment 2

[0034] Embodiment 2: the preparation of o-methoxycarbonylbenzenesulfenyl chloride

[0035]

[0036] Dissolve 5g (16.3mmol) of 2,2'-dithiodibenzoic acid in 37.5mL of anhydrous methanol, stir, slowly add 1.5mL of concentrated sulfuric acid dropwise, and heat to reflux for 72h. Cool to room temperature, remove excess methanol in vacuo, neutralize the concentrated solution with saturated sodium carbonate solution, bring the pH value to 7-8, extract the organic layer with ethyl acetate, wash with saturated brine, dry over magnesium sulfate, and concentrate in vacuo to obtain gray 2 , 4.5 g of solid methyl 2'-dithiodibenzoate (yield 82.5%).

[0037] The method of reference example 1 can prepare o-methoxycarbonylbenzenesulfenyl chloride.

[0038] Likewise, o-ethoxycarbonylbenzenesulfenyl chloride can be prepared.

Embodiment 3

[0039] Embodiment 3: the preparation of o-nitrobenzene sulfenyl chloride

[0040]

[0041] 1.93g (84mmol) of sodium metal was carefully and slowly added to 50mL of absolute ethanol, and after the reaction was completed, 10.33g (83mmol) of benzyl mercaptan dissolved in 25mL of absolute methanol was added. Then 13.13g (83mmol) o-nitrochlorobenzene was added dropwise, heated to reflux for 1h, cooled to room temperature, and suction filtered to obtain a yellow solid, which was then recrystallized with methanol to obtain 18.39g of 2-nitrophenylbenzyl sulfide (yield 90.3 %).

[0042] Dissolve 6.8g (50mmol) of sulfonyl chloride in 25mL of chloroform, and slowly add it dropwise to 12.2g (50mmol) of 2-nitrophenylbenzyl sulfide in 80mL of chloroform under stirring at room temperature. After the dropwise addition, the temperature was raised to 45°C. At this time, the reactants were completely dissolved, and the reaction was controlled at this temperature for 0.5 h. The solvent was re...

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PUM

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Abstract

The invention relates to a heterocyclic asymmetric aromatic dithioether compound and application thereof in herbicide preparation. As shown as in the formula (I), the compound has inhabitation effect to arabidopsis thaliana acetolactate synthase (AHAS) in vitro, has inhabitation effect to rape root length in vivo, has weeding effect for rape and redroot amaranth in potted plant tests, and can be used for preparing novel herbicides containing targeted AHAS. In the formula (I), when X represents S, R1 represents H, C1-C3 alkyl, C1-C3 acylamino, phenyl, hydroxylphenyl phenyl and ortho-C1-C3 alkoxy phenyl, R2 represents H, ortho-nitryl or para-nitryl, ortho-halogen or para-halogen, ortho-C1-C3 alkyl or para-C1-C3 alkyl, ortho-C1-C3 carbalkoxy, para-C1-C3 alkoxy and 3,4-benzo; and when X represents O, R1 represents H, phenyl, hydroxylphenyl phenyl, ortho-C1-C3 alkoxy phenyl, 4-pyridyl and 3-pyridyl, and R2 represents H, ortho-nitryl, para-C1-C3 alkyl and ortho-C1-C3 carbalkoxy.

Description

technical field [0001] The present invention relates to a class of heterocycle-containing asymmetric aromatic disulfide compounds and their use in the preparation of herbicides, in particular to the ability of such compounds to inhibit acetolactate synthase (acetohydroxyacid synthase) in vitro (in vitro). , AHAS), in vivo (in vivo) inhibitory effect on rapeseed root growth, and herbicidal effect on rapeseed and Amaranthus retroflexus in pot experiments. Background technique [0002] In today's world, overpopulation has caused severe food shortages, and due to the requirements of environmental protection, humans need herbicides to continue to function, but at the same time, they will not cause pollution and negative effects on the environment, and are safe for humans and animals. Therefore, it is an important research and development strategy for herbicides to search for specific targets that are not available in humans and animals for the design of pesticide molecules. [0...

Claims

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Application Information

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IPC IPC(8): C07D271/07C07D285/08A01N43/836A01P13/00
Inventor 王建国王伟民尚君李永红牛聪伟李正名
Owner NANKAI UNIV
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