Fluorocyanogen-containing pyrethroid compound and synthesis method and application thereof

A technology for pyrethroids and compounds, which is applied in the field of cyhalothrin-containing pyrethroids and their synthesis, and achieves the effects of simple and easy processing of process routes and wastes, reduced toxicity and biological resistance, and high product yields

Inactive Publication Date: 2010-11-10
BESTCHEN GUIYANG
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] where R 1 , R 2 Can be -H, -CF 3 or -CH 3 (EPA0638543, EPA0779269 etc.) this class compound is all used as insecticide, and has shown good insec

Method used

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  • Fluorocyanogen-containing pyrethroid compound and synthesis method and application thereof
  • Fluorocyanogen-containing pyrethroid compound and synthesis method and application thereof
  • Fluorocyanogen-containing pyrethroid compound and synthesis method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Example Embodiment

[0088] Example 1.1S-cis(Z)-2,2-dimethyl-3-(2-fluoro-2-cyano-1-vinyl)-cyclopropanecarboxylic acid or 1S-cis(Z)-2, 2-Dimethyl-3-(2-fluoro-2-cyano-1-vinyl)-cyclopropane acid chloride

[0089] (1) Preparation of 1S-cis(Z)-2,2-dimethyl-3-(2-fluoro-2-cyano-1-vinyl)cyclopropanecarboxylic acid

[0090] 0.5g of p-toluenesulfonic acid (PTSA) was added to dissolve 6.00g of 1R-cis(Z)-2,2-dimethyl-3-(2-fluoro-2-cyano-1-vinyl)cyclopropane Carboxy-1,1-dimethylethyl ester and 50 ml of toluene. The reaction was continued until heated to reflux at 120°C. Then cooled to 20 degrees, diluted with isopropyl ether, washed with water, dried, filtered and concentrated to obtain 4.60g of 1S-cis(Z)-2,2-dimethyl-3-(2-fluoro-2-cyano- 1-vinyl)cyclopropanecarboxylic acid.

[0091] (2) Preparation of 1S-cis(Z)-2,2-dimethyl-3-(2-fluoro-2-cyano-1-vinyl)-cyclopropane acid chloride

[0092] 1ml DMF (N,N-dimethylformamide) and 4.5ml (COCl) 2 (thionyl chloride) was added to 0°C to dissolve 4.60 g of 1S-cis(Z...

Example Embodiment

[0093] Example 2.1 R-trans(E)-2,2-dimethyl-3-(2-fluoro-2-cyano-1-vinyl)-cyclopropanecarboxylic acid or 1R-trans(E)-2, 2-Dimethyl-3-(2-fluoro-2-cyano-1-vinyl)-cyclopropane acid chloride:

[0094] (1) Preparation of 1R-trans(E)-2,2-dimethyl-3-(2-fluoro-2-cyano-1-vinyl)-cyclopropanecarboxylic acid:

[0095] 1.2 g of p-toluenesulfonic acid (PTSA) was added dissolved in 14.15 g of 1R-trans(E)-2,2-dimethyl-3-(2-fluoro-2-cyano-1-vinyl)cyclopropane Carboxy-1,1- dimethyl ethyl ester and 140ml of toluene. The reaction was continued until heated to reflux at 120°C. Then it was cooled to 20°C, diluted with 250ml of isopropyl ether, washed with water, dried, filtered and concentrated to obtain 11.32g of 1R-trans(E)-2,2-dimethyl-3-(2-fluoro-2-cyano- 1-vinyl)cyclopropanecarboxylic acid.

[0096] (2) Preparation of 1R-trans(E)-2,2-dimethyl-3-(2-fluoro-2-cyano-1-vinyl)-cyclopropane acid chloride:

[0097] 3ml DMF and 10ml (COCl) 2 It was added to 0°C and dissolved in 10 g of 1R-trans(E)2,...

Example Embodiment

[0099] Synthesis of Example 3 Compound (X1)

[0100] In a 500ml four-necked reaction flask, put 31.0g of 1-ethynyl-2-methylpent-2-enol and 25.0g of pyridine, dissolve in 200ml of toluene, stir evenly, and dropwise add 3- (2-Fluoro-2-cyano-1-vinyl)-2,2-dimethylcyclopropanecarboxylic acid chloride 56.0 g was added dropwise, and the temperature was raised to 25° C. to react for 2 hours. Wash twice with 150ml 10% hydrochloric acid followed by 150ml 10% NaHCO 3 Wash twice, separate the toluene layer and heat at 0.08Mpa to remove the solvent toluene to obtain -1-ethynyl-2-methylpent-2-enyl-3-(2-chloro-3,3,3-tri Fluoroallyl)-2,2-dimethylcyclopropanecarboxylate, the weight is 65.7 g, the content is 92.3%, and the yield is 83.9%.

[0101]

[0102] IR spectrum shows υ-c=o 1750cm -1 Strong absorption peak at υ-c-o-c-1180cm -1 and 1160cm -1 The two strong peaks of , indicate the presence of ester groups in the product; υ-c=o at 1720cm -1 The strong broad peaks on the left and rig...

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Abstract

The invention discloses a fluorocyanogen-containing pyrethroid compound and a synthesis method and an application thereof, which belong to the technical field of organic pesticides. The compound has a general structural formula (I) shown as the accompanying drawing, and in the general structural formula (I), R represents compounds applicable to the alcohol part contained in the conventional pyrethroid, which also include various stereoisomer forms thereof and the mixture of various stereo-configured compounds thereof. The invention also relates to an active component containing the fluorocyanogen-containing pyrethroid compound (I), which is used as an effective agent for controlling harmful insects, and a method for producing the ester compound (I). The invention discloses the application of the compound and a pesticidal mixture containing the compound as the active component in controlling pests.

Description

technical field [0001] The invention relates to a fluorine-containing cyanide pyrethroid compound and a synthesis method and application thereof, belonging to the technical field of organic insecticidal pyrethroids. Background technique [0002] Pyrethroids are lipophilic organic compounds. Pyrethroids are all obtained from natural pyrethrum flowers. They show strong insecticidal activity, which is based on the effect of sodium ion channels on the nerve membranes of pests. Such a powerful insecticidal activity. [0003] [0004] where R 1 , R 2 Can be -H, -CF 3 or -CH 3 (EPA0638543, EPA0779269 etc.) this class compound is all used as insecticide, and has shown good insecticidal activity, yet along with use dosage increases, also has shown such as effect, dosage, the scope of control insect pest, Toxicity and other discomfort issues. Therefore, we must constantly develop new insecticides that have been modified and improved in the main structure. Contents of the in...

Claims

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Application Information

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IPC IPC(8): C07C255/31C07D233/72C07C253/30A01N53/10A01N53/04A01N53/06A01P7/04A01P7/02
Inventor 黄锐强王俊李国江杨书翰
Owner BESTCHEN GUIYANG
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