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Fluorinated oxa or thia heteroarylalkylsulfide derivatives for combating invertebrate pests

An alkyl, animal-based technology for use in the field of alkyl sulfide compounds or their enantiomers or veterinarily acceptable salts capable of addressing food supply and property economic losses, destruction of growing and harvested crops, attack Issues with wooden houses and commercial structures

Active Publication Date: 2015-03-11
BOEHRINGER INGELHEIM ANIMAL HEALTH USA INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Invertebrate pests and especially arthropods and nematodes destroy growing and harvested crops and attack wooden houses and commercial structures causing large economic losses to the food supply and properties

Method used

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  • Fluorinated oxa or thia heteroarylalkylsulfide derivatives for combating invertebrate pests
  • Fluorinated oxa or thia heteroarylalkylsulfide derivatives for combating invertebrate pests
  • Fluorinated oxa or thia heteroarylalkylsulfide derivatives for combating invertebrate pests

Examples

Experimental program
Comparison scheme
Effect test

preparation example

[0612] The product was characterized by HPLC-MS (High Performance Liquid Chromatography Mass Spectrometry). HPLC was performed using an analytical RP-18e column (Chromolith Speed ​​ROD from Merck KgaA, Germany) operating at 40°C. 0.1% by volume of trifluoroacetic acid / water mixture and 0.1% by volume of trifluoroacetic acid in acetonitrile were used as mobile phase; flow rate: 1.8 mL / min and injection volume: 2 μl.

[0613] The following notations used in this document are defined as follows:

[0614] n-BuLi

Embodiment 7

[0615] Representative embodiment 7, the preparation scheme of 8 and 9:

[0616]

[0617] Preparation of [2-(trifluoromethyl)-5-{1-[2-(trifluoromethylthio)ethylthio]ethyl}-1,3,4-thiadiazole (7, corresponding to implementation Example I1-1)]

[0618] To a stirred solution of hydrazide 6 (0.55 g, 1.59 mmol) in xylene (20 mL) was added Lawesson's reagent (0.64 g, 1.59 mmol) at room temperature. The mixture was then stirred and heated at 120 °C for 2 h and reflux for 18 h. The solvent was removed in vacuo; the crude residue was purified by column chromatography (silica gel, eluent: hexane / EtOAc, gradient 9:1-8:2) to afford the title compound (0.28 g, 51%) as a butter.

[0619] Preparation of [2-(trifluoromethyl)-5-{1-[2-(trifluoromethylthio)ethylsulfinyl]ethyl}-1,3,4-thiadiazole (8, corresponding In embodiment I1-3)]

[0620] To stirred and cooled (0°C) anhydrous CH 2 Cl 2 To a solution of thiadiazole 7 (0.50g, 1.46mmol) in (10ml) was added m-CPBA (77%, 0.39g, 1.75mmol) an...

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PUM

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Abstract

The invention relates to alkylsulfide derivatives compounds of formula I as hereunder depicted or the enantiomers or veterinarily acceptable salts thereof which are useful for combating or controlling invertebrate pests, in particular arthropod pests and nematodes. The invention also relates to methods for controlling invertebrate pests by using these compounds and to plant propagation material and to agricultural and veterinary compositions comprising said compounds. wherein U, R1, R2, R3U, X, n and p are defined as in the description.

Description

【Technical field】 [0001] The present invention relates to alkyl sulfide compounds or enantiomers or veterinarily acceptable salts thereof, which are useful for combating or controlling invertebrate pests, especially arthropod pests and nematodes. The invention also relates to methods of controlling invertebrate pests by using these compounds and to plant propagation material and to agricultural and veterinary compositions comprising said compounds. 【Background technique】 [0002] Invertebrate pests and especially arthropods and nematodes destroy growing and harvested crops and attack wooden houses and commercial structures causing large economic losses to the food supply and properties. While a large number of insecticides are known, due to the ability of target pests to develop resistance against said agents, there is a continuing need for new agents for use against invertebrate pests, especially insects, arachnids and nematodes. [0003] WO 2009 / 075080, WO 2009 / 028727, WO...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D285/12A01N43/824A61K31/433A61P33/00
CPCA01N43/66A01N43/08C07D307/80C07D307/40C07D235/12C07D261/08A01N43/60C07D257/04A01N43/10C07D209/10C07D249/08C07D277/26A01N43/54A01N43/40C07D285/12C07D333/54A01N43/647C07D213/32C07D237/08A01N43/50C07D333/18C07D307/38C07D333/56A01N43/56A01N43/62C07D213/34A01N43/46C07D271/06C07D307/79C07D263/32C07D251/16A01N43/72A01N43/22C07D207/325C07D209/12A01N43/78A01N43/58C07D239/20A01N43/82C07D233/66A01N43/713A01N43/80A61P33/00A61P33/14
Inventor S·泽格尔R·保利尼S·格罗斯C·拜尔M·波尔曼H·M·M·巴斯蒂安斯M·莱克D·L·库尔博斯顿D·D·安斯鲍赫S·汤普森V·萨尔加多
Owner BOEHRINGER INGELHEIM ANIMAL HEALTH USA INC
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