Cyclopropane carboxylic ester type compound, and preparation and application of same

A technology of tertiary amine compounds and compounds, applied in the field of pesticides

Active Publication Date: 2013-08-14
LIANBAO CROP TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The prior art discloses a variety of pyrethroid compounds, such as pyrethrin, deltamethrin, fenvalerate, etc., although these compounds have good insecticidal activity, but with long-term continuous single use, pests Resistance to pesticides has developed, necessitating the development of new compounds

Method used

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  • Cyclopropane carboxylic ester type compound, and preparation and application of same
  • Cyclopropane carboxylic ester type compound, and preparation and application of same
  • Cyclopropane carboxylic ester type compound, and preparation and application of same

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0060] In a reaction flask equipped with a thermometer and a stirrer, add 24.75g of 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropanecarboxylic acid and 200g of tetra Carbon chloride, after stirring evenly at room temperature, add dropwise a carbon tetrachloride solution containing bromine under 20°C, the carbon tetrachloride solution containing bromine is formed by dissolving 16.5g of bromine in 50g of carbon tetrachloride ; Then add 0.5g triethylamine, stir the reaction at room temperature for 8 hours, get 1-(1,2-dibromo-2-chloro-3,3,3-trifluoro-1-propenyl) after removing the solvent -2,2-Dimethylcyclopropanecarboxylic acid;

[0061] In a reaction flask equipped with a thermometer and a stirrer, add 32.84g of 1-(1,2-dibromo-2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethyl Cyclopropanecarboxylic acid, 150mL dichloromethane and 1mL dimethylformamide, add 10g thionyl chloride dropwise at room temperature, heat up to reflux, stir and react under reflux for 3 hou...

Embodiment 2

[0065] Put 26.6g of 3-(2-chloro-3,3,3-trifluoro-1-propenyl)-2,2-dimethylcyclopropaneyl chloride, 100g of tetrachloride Carbon and 0.3g triethylamine, below 20 ℃, add dropwise the carbon tetrachloride solution containing bromine, the carbon tetrachloride solution containing bromine is formed by dissolving 16.5g bromine in 50g carbon tetrachloride, After that, it was stirred at room temperature for 4 hours, and the solvent was removed to obtain the compound having the structure of formula (II-a), with a content of 96% and a yield of 95%.

[0066] In a reaction flask equipped with a thermometer and a stirrer, put 22g of 3-phenoxy-4-fluorobenzaldehyde, 100g of benzene, 8.2g of potassium cyanide, 30g of water and 1g of tetrabutylammonium bromide, stir evenly, and cool down to Below 15°C, add 43.8g of the above-prepared compound with the structure of formula (II-a) dropwise, after the dropwise addition, stir and react at room temperature for 10 hours, wash the obtained reactant with...

Embodiment 3

[0069] In a 1000mL reaction flask equipped with a thermometer and a stirrer, add 49g of crude oil of kaufthrin with a purity of 93%, 200g of carbon tetrachloride and 1g of triethylamine, and drop carbon tetrachloride containing bromine below 20°C Solution, the carbon tetrachloride solution containing bromine is formed by dissolving 16.5g bromine in 50g carbon tetrachloride, and the dropwise addition is completed in about 2 hours. Afterwards, the reaction was stirred at room temperature for 48 hours, and the compound with the structure of formula (I-a) was obtained after removing the solvent, with a content of 93% and a yield of 94%.

[0070] The compound having the structure of formula (I-a) was tested, and the result showed that it had the structure of formula (I-b).

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Abstract

The invention provides a cyclopropane carboxylic ester type compound having the structure shown as the formula (I), and a preparation and the application of the same. The cyclopropane carboxylic ester type compound can be used for preventing and controlling agricultural pests, especially lepidoptera pests, Homoptera pests, thysanoptera pests or coleopteran pests, such as beet armyworm, prodenia litura, cabbage caterpillar, plutella xylostella, cotton bollworm, oriental tobacco budworm, imported cabbageworm, snout moth's larva, aphid, armyworm, plant hopper, aleyrodidae, leafhopper, thrips or Phyllotreta vittata Fabricius. According to the invention, beta-cyfluthrin is used as a control, the effect of preventing and controlling the cotton bollworm and the aphid of the compound shown as formula (I) provided by the invention is tested, and the result shows that the compound provided by the invention has better prevention and control effect on the cotton bollworm and the aphid than beta-cyfluthrin.

Description

technical field [0001] The invention relates to the technical field of pesticides, in particular to a cyclopropane carboxylate compound, its preparation method and its application. Background technique [0002] Pyrethroid compounds are a class of biomimetic synthetic insecticides that can be used for a variety of pests and have high insecticidal activity. Pyrethroid compounds have the characteristics of high efficiency, low toxicity, low residue and good environmental compatibility, and have been widely used in the field of pest control. [0003] The prior art discloses a variety of pyrethroid compounds, such as pyrethrin, deltamethrin, fenvalerate, etc., although these compounds have good insecticidal activity, but with long-term continuous single use, pests Resistance to pesticides has developed, necessitating the development of new compounds. Contents of the invention [0004] In view of this, the technical problem to be solved by the present invention is to provide a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C255/39C07C253/30A01N53/08A01P7/04
Inventor 王洲卢桂鲜
Owner LIANBAO CROP TECH
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