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2-chloro-benzoate compound and application thereof

A technology of ester compounds and chlorobenzoic acid, applied in the fields of application, organic chemistry, biocides, etc., can solve unrelated problems and achieve the effect of outstanding herbicidal activity

Active Publication Date: 2013-03-27
SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In the prior art, there is no reference to 2-chloro-5-(2,6-dichloro-4-(trifluoromethyl)phenoxy)benzoic acid (alkoxycarbonylalkyl)esters as shown in the present invention Compounds and their applications

Method used

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  • 2-chloro-benzoate compound and application thereof
  • 2-chloro-benzoate compound and application thereof
  • 2-chloro-benzoate compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0067] Embodiment 1: the synthesis of compound 2

[0068]

[0069] Add 25 grams of S-lactic acid (0.2 mole), methanol (32 grams, 1 mole), and 100 milliliters of benzene in sequence in a 500 milliliter reaction flask, then add 1 milliliter of concentrated sulfuric acid, heat to reflux, and use a water separator to separate the generated water, heated to reflux for 12 hours and the reaction was basically complete. The solvent was removed under reduced pressure to obtain a black oil. Distilled under reduced pressure to obtain 13.5 g of S-lactate methyl ester as a colorless liquid with a yield of 65%.

[0070]

[0071] In a 250 ml reaction flask, 3.47 grams of 2-chloro-5-(2,6-dichloro-4-(trifluoromethyl)phenoxy)benzoic acid (9 mmoles, prepared according to US4388472 method), Dichloromethane (30 ml), 2.62 g (18 mmol) of oxalyl chloride was added dropwise, and then 1 drop of DMF was added, stirred at room temperature for 5 hours, and desolvated under reduced pressure to obta...

Embodiment 2

[0074] Embodiment 2: the synthesis of compound 3

[0075]

[0076] 1.61 g (15.5 mmol) of S-methyl lactate, 2.98 g (15.53 mmol) of p-toluenesulfonyl chloride and dichloromethane (50 ml) were added successively in a 100 ml reaction flask, and 1.88 g of triethylamine ( 18.6 mmol), stirred at room temperature for 24 hours, and precipitated under reduced pressure. , the residue was purified by column chromatography (eluent was ethyl acetate:petroleum ether=1:5), to obtain 1.99 g of S-(2-p-toluenesulfonate)-methyl propionate, colorless oil, yield 50%.

[0077] Add 0.77 g (2 mmol) of 2-chloro-5-(2,6-dichloro-4-(trifluoromethyl)phenoxy)benzoic acid, N,N-di Methylformamide (20 ml), 0.42 g (3 mmol) of potassium carbonate, and 0.57 g (2 mmol) of S-(2-p-toluenesulfonyl)-propionic acid methyl ester were stirred at room temperature for 1 hour. The reaction solution was poured into 50 ml of water, extracted with 200 ml of ethyl acetate, the organic layer was washed with water and satur...

Embodiment 3

[0078] Embodiment 3: the synthesis of compound 4

[0079]

[0080] Add 0.81 g (2 mmol) of 2-chloro-5-(2,6-dichloro-4-(trifluoromethyl)phenoxy)benzoyl chloride, S-lactate ethyl Ester 0.26 g (2.2 mmol, obtained with reference to the preparation method of S-lactate methyl ester in Example 2) and methylene chloride (20 ml), was added dropwise with 0.24 g of triethylamine (2.4 mmol), stirred at room temperature for 1 hour . The reaction solution was poured into 20 ml of water, extracted with 150 ml of ethyl acetate, the organic layer was washed successively with saturated sodium carbonate solution, water, and saturated brine, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and the residue was purified by column chromatography (The eluent is ethyl acetate:petroleum ether=1:20), and 0.74 g of compound 4 was obtained as a yellow oil, with a yield of 76%. The normalized content of S-body (retention time: 5.790min) was 99.9%, and no R-body was detected....

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Abstract

The invention discloses a 2-chloro-benzoate compound which has a novel structure and is shown as the general formula (I), wherein R1 is selected from H or methyl, R2 is selected from H or methyl, and R3 is selected from C1-C6 alkyl or benzyl. When R1 is selected from H and R2 is selected from methyl, carbon atoms connected with R1 and R2 in the general formula are in an S or R structural type. Or the invention provides a compound which contains different contents of S and R structural types. The compound which is shown as the general formula (I) has extraordinary weeding activity after seedling.

Description

technical field [0001] The invention belongs to the field of herbicides, and in particular relates to a 2-chlorobenzoate compound and an application thereof. Background technique [0002] Due to the succession and change of weed populations and the emergence and rapid development of resistance to chemical pesticides, people's awareness of ecological environment protection has been continuously strengthened. The importance of the issue of whereabouts continues to increase. With the gradual reduction of the world's arable land, the continuous growth of the population and the increase in the demand for food, people are forced to rapidly develop agricultural production technology, improve and improve the farming system, and need to continuously invent new and improved herbicidal compounds and compositions. [0003] US3957852A1 discloses the following benzoate compounds: [0004] [0005] Among them, R is selected from C 1 -C 5 Alkyl, alkali metal ion, amine; representativ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C69/92A01N37/40A01P13/00
Inventor 李斌于海波崔东亮杨辉斌孔宝祥吴鸿飞
Owner SHENYANG SINOCHEM AGROCHEMICALS R&D CO LTD
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