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Fluorine-contained o-amino thiobenzamide type compound and application thereof

A technology of o-aminothiobenzamides and compounds, which is applied in the field of fluorine-containing antho-aminothiobenzamides, can solve the problems that fluorine-containing antho-aminothiobenzamides have not been disclosed, and achieve improvement Fat-soluble, easy to synthesize, and good environmental compatibility

Active Publication Date: 2015-06-17
河南豫珠恒力生物科技有限责任公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Although the compounds disclosed in the above-mentioned patents have similarities with the compounds of the present invention, in the prior art, the fluorine-containing anthranilothiobenzamide compounds (Formula I) described in the present invention have not been disclosed

Method used

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  • Fluorine-contained o-amino thiobenzamide type compound and application thereof
  • Fluorine-contained o-amino thiobenzamide type compound and application thereof
  • Fluorine-contained o-amino thiobenzamide type compound and application thereof

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0029] The preparation of example 1, compound 1

[0030] (1) Synthesis of difluoroethanol methylsulfonate

[0031] CF 2 HCH 2 OH+CH 3 SO 2 Cl→CHF 2 CH 2 OSO 2 CH 3

[0032] Add 12.15g (0.15mol) difluoroethanol and 60mL ethyl acetate to a 250mL reaction flask, dropwise add 16.5g (0.165mol) of triethylamine, control the temperature in an ice bath below 10°C, add dropwise 18.9g of methanesulfonyl chloride ( 0.165mol), after dropping, warmed up to room temperature, stirred for 4h, filtered with suction, washed the filter cake with 20mL×2 ethyl acetate, and evaporated the filtrate to dryness to obtain a colorless and transparent oil, which was directly used in the next reaction.

[0033] (2) Synthesis of ethyl 1-(3-chloropyridin-2-yl)-3-difluoroethoxy-1H-pyrazole-5-carboxylate

[0034]

[0035] Add 26.7g (0.1mol) of 1-(3-chloro-2-pyridyl)-3-hydroxy-1H-pyrazole-5-carboxylic acid ethyl ester (see WO2003 / 015519 for synthesis) and 150mL of acetonitrile into a 250mL reactio...

example 2

[0048] Example 2, the synthesis of compound 10

[0049] (1) Synthesis of ethyl 1-(3,5-dichloropyridin-2-yl)-3-difluoroethoxy-1H-pyrazole-5-carboxylate

[0050]

[0051] Add 30.4 g (0.1 mol) of 1-(3,5-dichloro-2-pyridyl)-3-hydroxy-1H-pyrazole-5-carboxylic acid ethyl ester (see CN101747318A for synthesis), acetonitrile 150mL, K 2 CO 3 16.56g (0.12mol), 20.8g (0.13mol) of difluoroethanol methylsulfonate prepared in step (1), heated to reflux for 8h until the raw material completely disappeared, cooled to room temperature, filtered with suction, and used 30mL × 2 washes with acetonitrile, and the filtrate was evaporated to dryness to obtain 30.8 g of oily substance, with a yield of 84.3%.

[0052] (2) Synthesis of 1-(3,5-dichloropyridin-2-yl)-3-difluoroethoxy-1H-pyrazole-5-carboxylic acid

[0053]

[0054] Add 36.6g (0.1mol) of ethyl 1-(3,5-dichloropyridin-2-yl)-3-difluoroethoxy-1H-pyrazole-5-carboxylate into 250mL reaction flask and dissolve in 100mL methanol The mixed s...

example 3

[0070] Example 3, the synthesis of compound 19

[0071] (1) Synthesis of 2-amino-3,5-dibromobenzoic acid

[0072]

[0073] Add 13.7g (0.1mol) of 2-aminobenzoic acid and 80mL of acetic acid to a 250mL reaction flask, add 16g (0.1mol) of bromine dropwise at room temperature, stir at room temperature for 3h until the color of bromine fades, filter with suction and wash with water to obtain a white solid 28.6g, yield 96.3%.

[0074] (2) Synthesis of 6,8-dibromoisatoic anhydride

[0075]

[0076] Add 29.7g (0.1mol) of 2-amino-3,5-dibromobenzoic acid, 180mL ethyl acetate, and 5 drops of pyridine into a 250mL reaction flask, add 19.8g (0.67mol) of solid phosgene under ice-cooling, and heat up to 30~35°C, keep warm for 4h, reflux for 2h to drive out phosgene, cool down to room temperature, filter with suction, wash with water to obtain 26.9g of white solid, yield 83.2%.

[0077] (3) Synthesis of 2-amino-3,5-dibromo-N-allylbenzamide

[0078]

[0079] Add 32.3g (0.1mol) of ...

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Abstract

The invention discloses a fluorine-contained o-amino thiobenzamide type compound with a novel structure. The structure of the compound is shown in the general formula I: according to the general formula I, R1 is methyl, Cl or Br; R2 is Cl or Br; R3 is methyl, ethyl, isopropyl, allyl, or tertiary butyl; R4 is Cl or H. The compound adopting the general formula I has excellent pesticidal capactivity, and can be used for prevention and treatment of agricultural or forestry pests.

Description

technical field [0001] The invention belongs to the field of agricultural insecticides, and relates to a fluorine-containing o-aminothiobenzamide compound and an application thereof. Background technique [0002] The resistance of pests is the main source of their difficulty in control, and the development of new control agents is an important way to control resistance. Anthranilamide compounds (ryanodine receptor inhibitors) are effective insecticides developed in recent years to control Lepidoptera pests. PCT patent application WO2003 / 015519 discloses the following compounds (KC) having pesticidal activity. [0003] [0004] PCT patent application WO2006 / 023783 discloses the following fluorochemicals with insecticidal activity: [0005] [0006] CN101967139A discloses fluorine-containing compounds that are effective against pests of Lepidoptera, Semi-Lepidoptera and Homoptera: [0007] [0008] Although the compounds disclosed in the above patents have similari...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/04A01N43/56A01P7/04
Inventor 许良忠田帅刘春风陈慰燕王明慧
Owner 河南豫珠恒力生物科技有限责任公司