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Aryl sulfide containing benzylamine structure and synthesis method and application thereof

A technology containing benzylamine and sulfide, applied in the field of pesticides, can solve the problems of low killing activity, poor control effect of spider mites, unsatisfactory acaricidal activity and the like

Active Publication Date: 2020-10-27
SHANDONG KANGQIAO BIO TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] It is known that the active compounds described in the above-mentioned documents still have relatively low killing activity when controlling pests, especially mites, and their acaricidal activity is often unsatisfactory especially at low application rates, and The control effect on spider mites that have acquired drug resistance is even worse, so there is still an urgent need for new drugs with high efficiency, low toxicity, and excellent killing effect on resistant mites in agricultural production

Method used

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  • Aryl sulfide containing benzylamine structure and synthesis method and application thereof
  • Aryl sulfide containing benzylamine structure and synthesis method and application thereof
  • Aryl sulfide containing benzylamine structure and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0126] Preparation of N-(4-chloro-3-fluorobenzyl)-2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)aniline (Compound 249)

[0127] Step 1: Preparation of 4-fluoro-2-methyl-5-nitrobenzenesulfonyl chloride

[0128]

[0129] At room temperature, chlorosulfonic acid (34.95g, 30mmol) was added to a 250mL round bottom flask, 2-fluoro-4-methylnitrobenzene (15.5g, 10mmol) was slowly added to the reaction flask in 4 batches, and the reaction The liquid has a significant exotherm. After the addition, the reaction flask is transferred to 60 degrees Celsius and heated, and the reaction is basically completed after 2 hours. The reaction solution was added to 500 mL of ice-water mixture, 400 mL of dichloromethane was added, and the liquid was separated after rapid extraction. The organic phase was again added with 300 mL of water, and the organic phase was evaporated to dryness after extraction and separation. Yellow solid 16.5g (yield 64.45%).

[0130] Step 2: Preparation of 1,2-bis(4-fluoro-2-m...

Embodiment 2

[0153] Preparation of 2-fluoro-N-(3-fluorobenzyl)-4-methyl-5-((2,2,2-trifluoroethyl)thio)aniline (compound 229)

[0154] Step 1: Preparation of 4-fluoro-2-methyl-5-nitrothiophenol

[0155] Place 4-fluoro-2-methyl-5-nitrobenzenesulfonyl chloride (0.15mol, 38.0g) in a 250ml single-necked flask, add 80ml of hydroiodic acid, the reaction system will turn black, stir and react at room temperature for 1 hour, then 80ml of saturated aqueous sodium sulfite solution was slowly added, and a yellow powdery solid appeared in the reaction system. The solid was filtered under reduced pressure and washed with water and dried to obtain 28.0 g of light yellow powder with a yield of 100%.

[0156] Step 2: Preparation of 4-fluoro-2-methyl-5-aminothiophenol

[0157] Dissolve 4-fluoro-2-methyl-5-nitrothiophenol (0.15mol, 28.0g) in absolute ethanol (280mL), add 10% palladium on carbon (1.0g, 50% water content) , Hydrogen replaces the gas in the reaction flask three times, and the reaction solution is sti...

Embodiment 3

[0166] Preparation of 2-fluoro-N-(3-methoxybenzyl)-4-methyl-5-((2,2,2-trifluoroethyl)thio)aniline (Compound 239)

[0167] Step 1: Preparation of N-(2-fluoro-4-methylphenyl)acetamide

[0168]

[0169] Dissolve 2-fluoro-4methyl aniline (125g, 1mol) in dichloromethane (1L), add triethylamine (111g, 1.1mol), cool to internal temperature 0 degrees Celsius in an ice salt bath, slowly add acetic anhydride dropwise (102g, 1mol), after the addition, the reaction solution was transferred to room temperature and the reaction was continued for 3 hours. 2L of water was added to the reaction solution, and the liquid was extracted. The organic phase was dried by adding anhydrous sodium sulfate and evaporated to dryness to obtain 162g white solid , The yield is 97.0%.

[0170] Step 2: Preparation of 5-acetamido-4-fluoro-2-methylbenzenesulfonyl chloride

[0171]

[0172] Add N-(2-fluoro-4-methylphenyl)acetamide (145g, 868mmol) into a 1L round bottom flask, set up an exhaust gas absorption device, and...

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PUM

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Abstract

The invention belongs to the technical field of pesticides, and particularly relates to aryl sulfide containing a benzylamine structure and a synthesis method and application of the aryl sulfide. Represented by the following compounds: or an agriculturally acceptable salt thereof. The compound as shown in the general formula I has an excellent effect on various harmful organisms, especially on tetranychus cinnabarinus, tetranychus urticae, tetranychus kanzawai, Panonchus citri Mc Gregor and the like, and can be used for preventing and treating various harmful mites.

Description

Technical field [0001] The invention relates to the technical field of pesticides, in particular to an aryl sulfide containing a benzylamine structure, and a synthesis method and application thereof. Background technique [0002] Patent documents WO9955668A, CN104995193A, CN105517995A, JP2015036377A, CN103664811B, US2017226107A, WO2018051252A, TW201127291A, CN108290886A, JP2011042611A, JP2011219419A, JP2015036377A and the like describe aryl sulfide oxide derivatives having harmful biological control effects. [0003] Among them, the following general formula compounds disclosed by Soda Corporation in the patent JP2011-42611A have acaricidal activity: [0004] [0005] Where A is oxygen or sulfur, R 5 C is substituted or unsubstituted 1-20 Alkyl groups, substituted or unsubstituted amino groups, nitrogen-containing heterocycles, etc. [0006] Insecticides (India) Co., Ltd. published in patent WO2018015852 (CN109803956A) the following general formula compounds have acaricidal activity: ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C323/36C07C317/36C07C319/20C07C315/04A01N41/12A01N41/10A01P7/02A01P7/04A01P5/00
CPCC07C323/36C07C317/36A01N41/12A01N41/10A01N33/10A01N33/18A01N37/34A01N37/44A01P7/02C07C319/14C07C315/02A01P7/04
Inventor 李宁柳英帅李先江肖建刘祥伟刘瑞宾盛国柱冯睿杰项效忠崔迎蕊陈瑜王世玲
Owner SHANDONG KANGQIAO BIO TECH CO LTD
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