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Cyan dihalogenation pyrazol amide series compound and preparation method and application thereof

A technology for cyanodihalogenated pyrazole amides and compounds is applied in the field of cyanodihalogenated pyrazole amides and their preparation, which can solve problems such as unpublished application performance, and achieve high insecticidal activity, insecticidal activity and the like. The effect of broad spectrum and strong systemic activity

Inactive Publication Date: 2016-03-02
邓方坤
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] The present invention changes the Cl or Br at the R2 position of KC into a cyano group, although the compound of the present invention is structurally similar to cyantraniliprole (CY, cyantraniliprole) and dihalogenated pyrazole amide (KC) However, the cyano-substituted cyanodihalopyrazole amide formula I compound and its application properties of the present invention have not been disclosed, and the cyano-substituted cyanodihalopyrazole amide formula I compound has relatively Stronger insecticidal activity and systemic activity of CY and KC

Method used

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  • Cyan dihalogenation pyrazol amide series compound and preparation method and application thereof
  • Cyan dihalogenation pyrazol amide series compound and preparation method and application thereof
  • Cyan dihalogenation pyrazol amide series compound and preparation method and application thereof

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Experimental program
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Effect test

Embodiment 1

[0027] The preparation of embodiment 1 compound 1,

[0028] (1) Synthesis of 1-(3-chloropyridin-2-yl)-3-bromo-4-chloro-1H-pyrazole-5-carboxylic acid ethyl ester

[0029]

[0030] Add 33.25g (0.1mol) 1-(3-chloropyridin-2-yl)-3-bromo-4,5-dihydro-1-H pyrazole-5-carboxylic acid ethyl ester and 100ml acetonitrile to the 250ml reaction flask , adding 27g (0.2mol) of sulfonyl chloride under stirring, refluxed for 4h, thin-layer chromatography TLC detected that the raw material disappeared, and the solvent was distilled off to obtain 30g of yellow oily liquid with a yield of 82%.

[0031] Among them, 1-(3-chloropyridin-2-yl)-3-bromo-4,5-dihydro-1H pyrazole-5-carboxylic acid ethyl ester references (Wang Yanjun, Zhang Dayong, Wu Xiaoming, Chlorantraniliprole Synthesis of [J]. Pesticides, 2010, (03): 170-174).

[0032] (2) Synthesis of 1-(3-chloropyridin-2-yl)-3-bromo-4-chloro-1H-pyrazole-5-carboxylic acid

[0033]

[0034] Add 36.6g (0.1mol) 1-(3-chloropyridin-2-yl)-3-bromo-4-c...

Embodiment 2

[0055] The synthesis of embodiment 2 compound 2

[0056] (1) Synthesis of 2-amino-5-cyano-N-ethyl-3-methylbenzamide

[0057]

[0058] Take 6-cyano-8-methyl-1H-benzo[d][1,3]oxazine-2,4-dione 2.0g (0.01mol), acetonitrile 20ml, triethylamine 2g (0.02mol) In a 50ml single-necked bottle equipped with a stirring magnet, add 4g (0.02mol) of ethylamine aqueous solution dropwise under stirring, stir at room temperature for 2h until the reaction is clear, distill off the solvent, extract the reaction with ethyl acetate three times, combine the organic phases and use It was washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was removed to obtain 1.5 g of a yellow solid with a yield of 62%.

[0059] (2) Synthesis of Compound 2

[0060]

[0061] Add 2.13g (0.01mol) 2-amino-5-cyano-N-ethyl-3-methylbenzamide to a 100ml reaction flask, 10ml acetonitrile, drop 3.92g (0.011mol) 1-(3-chloro A mixed solution of pyridin-2-yl)-3-bromo-4-chloro-1H-pyrazole-5-f...

Embodiment 3

[0063] The synthesis of embodiment 3 compound 4

[0064] (1) Synthesis of 2-amino-5-iodo-3-chlorobenzoic acid

[0065]

[0066] Put 5.2g (0.033mol) of 2-amino-3-chlorobenzoic acid in a 100ml reaction flask, add 30ml of DMF, add NIS iodide reagent (7.8g, 0.035mol) under stirring at room temperature, raise the temperature to 80°C for 2h, TLC After monitoring the completion of the reaction, the temperature was lowered to 30° C., the reaction solution was poured into ice water, stirred for 20 min, and filtered to obtain 8.9 g of a gray solid with a yield of 95%.

[0067] (2) Synthesis of 2-amino-5-cyano-3 chlorobenzoic acid

[0068]

[0069] 2-Amino-5-iodo-3-chlorobenzoic acid 4.37g (0.015mol) CuCN1.87g (0.021mol) in a 100ml reaction flask, add 50ml of DMF, the temperature rises to 145°C to react, keep the temperature for 5h, TLC detection After the reaction was complete, most of the solvent was removed under reduced pressure, 50ml of water and 5ml of ethylenediamine were ...

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Abstract

The invention discloses a cyan dihalogenation pyrazol amide series compound and a preparation method and application thereof. The general chemical molecular formula of the compound is C<17>H<7>N<6>O<2>Cl<2>BrR1R2, wherein R1 represents methyl, Cl or Br; R2 represents H, methyl, isopropyl, ethyl, allyl, butyl or isobutyl. The preparation method of the compound comprises the steps of treating triethylamine or pyridine as an acid binding agent, making substitued 2-amino-5-cyan-N-benzamide react with 1-(3chloropyridine)-2-group)-3-bromine-4-chlorine-1H-pyrazol-5-formyl chloride in acetonitrile at the temperature of 0-40 DEG C for two hours, and obtaining the compound; or treating acetonitrile or methylbenzene as solvent, conducting backflow for 3-4 hours, and obtaining the compound. The compound is used for pest control in sanitation, agriculture or forestry and is high in insecticidal activity and systemic property and wide in insecticidal spectrum.

Description

technical field [0001] The invention relates to the field of insecticides, in particular to a cyanodihalogenated pyrazole amide compound and a preparation method and application thereof. Background technique [0002] In 2000, DuPont reported a new type of cyantraniliprole (CY, cyantraniliprole) with systemic activity, which is a new type of ryanodine receptor inhibitory insecticide. The product has systemic activity and can extensively control Lepidoptera, Hemiptera and Coleoptera pests. The structural formula of compound cyantraniliprole (CY, cyantraniliprole) is: [0003] [0004] In the patent CN103232431 "a dihalogenated pyrazole amide compound and its application", a dihalogenated pyrazole amide compound (KC) is disclosed, the structural formula is: [0005] [0006] In the structural formula KC, R1 is methyl, Cl or Br; R2 is Cl or Br, and R3 is H, methyl, isopropyl, ethyl, or allyl. [0007] The present invention changes the Cl or Br at the R2 position of KC i...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/04A01N43/56A01P7/04
CPCC07D401/04A01N43/56
Inventor 邓方坤
Owner 邓方坤
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