N-benz-3-substituted amino pyrazoles compounds with insecticidal activity

A technology of aminopyrazoles and compounds, applied in the field of N-phenyl-3-substituted aminopyrazoles

Active Publication Date: 2009-01-07
HUNAN CHEM RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although there are many pesticides and insecticides on the market, there is still a need for new compounds that are more efficient, safe, economical, and have different modes of action

Method used

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  • N-benz-3-substituted amino pyrazoles compounds with insecticidal activity
  • N-benz-3-substituted amino pyrazoles compounds with insecticidal activity
  • N-benz-3-substituted amino pyrazoles compounds with insecticidal activity

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0062] The preparation method of compound 01 in Table 1.

[0063] Add 4.6g (10.5mmol) of the compound of formula (II) (X=SO) in Reaction Formula 1 into a three-necked flask with a condenser tube, then add 1.12g (20mmol) KOH and 10ml DMF, and drop in 2.3g ( 21mmol) of 1,3-transdichloropropene, after dropping, the solution turned from light yellow to brownish red, and reacted overnight at room temperature. The reactant was poured into 250ml of water for washing, extracted with ethyl acetate, and dried over anhydrous sodium sulfate. concentrate. Column chromatography (petroleum ether: ethyl acetate = 12:1) gave 2.1 g of a white powdery solid with a content of 95% and a yield of 38.96%. Melting point: 174.3~175.6℃

Embodiment 2

[0065] The preparation method of compound 02 in Table 1.

[0066] Add 4.6g (10.5mmol) of the compound of formula (II) (X=SO) in Reaction Formula 1 into a three-necked flask with a condenser tube, then add 1.12g (20mmol) KOH and 10ml DMF, and drop in 2.3g ( 21mmol) of 2,3-dichloropropene, after dropping, the solution turned from light yellow to deep yellow, and reacted overnight at room temperature. The reactant was poured into 250ml of water for washing, extracted with ethyl acetate, and dried over anhydrous sodium sulfate. concentrate. Column chromatography (petroleum ether: ethyl acetate = 20:1) yielded 2.3 g of off-white powdery solid, content 95.12%, yield 42.72%. Melting point: 168.4~169.5℃

Embodiment 3

[0068] The preparation method of compound 08 in Table 1.

[0069] Add 4.4g (10.5mmol) of the compound of formula (II) (X=S) in Reaction Formula 1 into a three-necked flask with a condenser tube, then add 1.12g (20mmol) KOH and 10ml DMF, and add 2.2g dropwise under stirring at room temperature (20mmol) (E) 1,3-dichloropropene, after dropping, react overnight at room temperature. The reactant was poured into 250ml of water for washing, extracted with ethyl acetate, dried over anhydrous sodium sulfate, and concentrated. Column chromatography (petroleum ether: ethyl acetate = 5:1) gave 2.3 g of a white solid with a content of 95% and a yield of 44.23%. Melting point: 121.5~123.0℃

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Abstract

The invention discloses an N-phenyl-3-substitution amino-pyrazole compound which is shown in a formular (1) and has the insecticidal activity, and a preparation method thereof.

Description

technical field [0001] The invention relates to N-phenyl-3-substituted aminopyrazole compounds with insecticidal activity and a preparation method. Background technique [0002] Pest control is very important in achieving efficient agriculture. Also pest control is important in forestry, greenhouse crops, ornamental plants, nursery crops, stored food and fiber products, livestock, household, and public health and animal care. Although there are many pesticides and insecticides on the market, there is still a need for new compounds that are more efficient, safe, economical and have different modes of action. [0003] Phenylpyrazoles are also a class of efficient and safe insecticides. In 1989, the French Rhone-Planck company developed the insecticide shown in formula i, and its trade name was "Regent". In 2000, the French Rhone-Planck company disclosed phenylpyrazoles with insecticidal activity in US 6015910, and found another pyrazole insecticide shown in formula ii, the ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D231/44C07D403/12A01N43/56A01N43/54A01P7/00
Inventor 柳爱平陈灿王永江陶贤鉴王晓光欧晓明刘兴平项军林雪梅黄明智
Owner HUNAN CHEM RES INST
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