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Fluorine-containing butenyl ester derivatives as well as preparation method and application thereof

A technology containing fluorobutene and derivatives is applied in the field of pesticides, which can solve the problems of invasion, damage to plant roots, and phytotoxicity of crops, and achieve the effects of improving crop growth and development, high safety performance, and good control effect.

Pending Publication Date: 2022-01-11
SHANDONG UNITED PESTICIDE IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Invertebrate pests, such as arthropods, nematodes or mites can destroy growing and harvested crops, causing serious losses to crop yields and harvests. The continuous generation of drug resistance requires continuous research and development of new insecticides to control or kill invertebrate pests, such as insects, spiders and mites; on the other hand, the growth of nematodes has its own particularity, and most In the soil, or parasitic in the plant, spread through the soil or seeds, mainly destroy the root system of the plant, or invade the plant organs of the above-ground part, affect the growth and development of the crops, and cause great economic losses in agriculture. Most nematicides penetrate through the epidermis of nematodes and play a poisonous role. Good nematocides have high toxicity to humans and animals. Some varieties have phytotoxicity to crops, which affects their application range.
[0003] Chinese patents CN106554334 and CN109020928 disclose the application of trifluorobutene ester compounds as nematocides, but they are not used to prevent or eliminate invertebrate pests or mites, so they have good pesticide activity, especially insecticide Insecticides, acaricides and nematicides that can prevent or kill various invertebrate pests are urgently needed to develop

Method used

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  • Fluorine-containing butenyl ester derivatives as well as preparation method and application thereof
  • Fluorine-containing butenyl ester derivatives as well as preparation method and application thereof
  • Fluorine-containing butenyl ester derivatives as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0216] 3,4,4-Trifluorobut-3-enylpropionate (Compound 2)

[0217]

[0218] At room temperature, dissolve 1.50g (0.02mol) propionic acid, 3.95g (0.021mol) 4-bromo-1,1,2-trifluoro-1-butene, 3.10g (0.022mol) anhydrous potassium carbonate in 25ml in acetonitrile. Reflux reaction for 24h. Suction. The solvent, acetonitrile, was evaporated from the filtrate under reduced pressure. The residue was dissolved in 25ml of dichloromethane, 20ml of water was added to the above solution, and the layers were separated. The organic layer was washed with 15 ml of saturated brine. Dry over anhydrous sodium sulfate. Concentrate under reduced pressure. Column chromatography (eluent: ethyl acetate: petroleum ether = 1:8) yielded 2.80 g of the product with a yield of 77%.

[0219] LC-MS [M+H]+=183.07, [M+Na]+=205.05, [M+K]+=221.02.

Embodiment 2

[0221] 3,4,4-Trifluorobut-3-enyl 5-oxo-2-o-tolyl tetrahydrofuran-3-carboxylate (compound 35)

[0222]

[0223] The first step reaction: preparation of 5-oxo-2-o-tolyltetrahydrofuran-3-carboxylic acid

[0224]At room temperature, add 2.40g (0.02mol) of o-tolualdehyde, 2.50g (0.025mol) of succinic anhydride, 5.98g (0.044mol) of anhydrous zinc chloride and 30ml of anhydrous 1,2 - dichloroethane. Stir and cool down to 2°C. 4.06 g (0.04 mol) of triethylamine was added dropwise to the above reaction liquid. Then the temperature was raised to 40°C, and the reaction was stirred for 12h. 20 ml of water was added to the above reaction solution and stirred, and 4.0 ml of concentrated hydrochloric acid was added thereto. Stir, let stand to separate layers, and extract the water layer with 20ml 1,2-dichloroethane. The organic layers were combined, washed with 30 ml of water, and the solvent was removed from the organic phase under reduced pressure. Toluene was recrystallized to ob...

Embodiment 3

[0230] 3,4,4-Trifluorobut-3-enyl 2-oxo-1-oxaspiro[4.5]-decane-4-carboxylate (compound 57)

[0231]

[0232] At room temperature, 2.97g (0.015mol) of 2-oxo-1-oxaspiro[4.5]-decane-4-carboxylic acid, 3.21g (0.017mol) of 4-bromo-1,1,2-trifluoro- 1-Butene, 2.35g (0.017mol) of anhydrous potassium carbonate were dissolved in 30ml of acetonitrile. Reflux reaction for 24h. Suction. The solvent, acetonitrile, was evaporated from the filtrate under reduced pressure. The residue was dissolved in 30 ml of dichloromethane, 20 ml of water was added to the above solution, and the layers were separated. The organic layer was washed with 15 ml of saturated brine. Dry over anhydrous sodium sulfate. Concentrate under reduced pressure. Column chromatography (eluent: ethyl acetate: petroleum ether = 1:8) yielded 3.72 g of the product with a yield of 81%.

[0233] LC-MS [M+H]+=307.12, [M+Na]+=329.1, [M+K]+=345.07.

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Abstract

The invention discloses fluorine-containing butenyl ester derivatives, which comprise a fluorine-containing butenyl ester compound, a stereoisomer, a racemate, a tautomer, a nitrogen oxide or an agronomically acceptable salt thereof. The derivatives provided by the invention contain a fluorobutenyl ester structure, can be used in agricultural pest control, can show very good activity on various pests, mites and nematodes, can obtain very good control effect at very low dosage of the compounds, and have the advantages of small dosage, high safety performance and no harm to crops; on the contrary, the compounds have good activity in the aspect of improving the growth and development of crops.

Description

technical field [0001] The present invention relates to the technical field of insecticides, in particular to a fluorine-containing butene ester derivative and its preparation method and application; the fluorine-containing butene ester derivative or the The compositions can control or control invertebrate pests, especially arthropod pests and nematodes. Background technique [0002] Invertebrate pests, such as arthropods, nematodes or mites can destroy growing and harvested crops, causing serious losses to crop yields and harvests. The continuous generation of drug resistance requires continuous research and development of new insecticides to control or kill invertebrate pests, such as insects, spiders and mites; on the other hand, the growth of nematodes has its own particularity, and most In the soil, or parasitic in the plant, spread through the soil or seeds, mainly destroy the root system of the plant, or invade the plant organs of the above-ground part, affect the gr...

Claims

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Application Information

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IPC IPC(8): C07C69/24C07C67/08C07D307/33C07D207/277C07D407/04C07D405/04C07D417/04C07C69/616C07D317/60C07C69/65C07C69/734C07C69/767C07C69/92C07D213/80C07D213/803C07D239/30C07D215/54C07D241/24C07D239/86C07D239/34C07D241/44C07D471/04A01P5/00A01P7/02A01P7/04A01N37/02A01N43/08A01N43/36A01N43/32A01N43/30A01N43/60A01N43/58A01N43/54A01N43/78A01N37/10A01N37/38A01N37/40A01N43/40A01N43/42A01N43/90A01G13/00A01G7/06
CPCC07C69/24C07D307/33C07D207/277C07D407/04C07D405/04C07D417/04C07C69/616C07D317/60C07C69/65C07C69/734C07C69/76C07C69/92C07D213/80C07D213/803C07D239/30C07D215/54C07D241/24C07D239/86C07D239/34C07D241/44C07D471/04A01N37/02A01N43/08A01N43/36A01N43/32A01N43/30A01N43/60A01N43/58A01N43/54A01N43/78A01N37/10A01N37/38A01N37/40A01N43/40A01N43/42A01N43/90A01G13/00A01G7/06
Inventor 唐剑峰赵宝修迟会伟吴建挺徐龙祥韩君赵恭文赵士胜
Owner SHANDONG UNITED PESTICIDE IND CO LTD