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Mixed compositions for controlling parasitic insects

A composition and technology for ectoparasites, applied in the directions of drug combinations, active ingredients of heterocyclic compounds, applications, etc., can solve problems such as difficulty in preventing and controlling drug-resistant ectoparasites

Inactive Publication Date: 2005-10-26
MEIJI SEIKA KAISHA LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, since these synthetic pyrethrin insecticides have been used for many years, some ectoparasites have acquired resistance, so the control of drug-resistant ectoparasites has become very difficult

Method used

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  • Mixed compositions for controlling parasitic insects
  • Mixed compositions for controlling parasitic insects
  • Mixed compositions for controlling parasitic insects

Examples

Experimental program
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Effect test

preparation example Construction

[0053] The preparation method of formula (I) compound

[0054] Compounds of formula (I) can be prepared, for example, according to the methods shown in Scheme I. For the preparation of these compounds, Japanese Patent Unexamined Publication No. 128355 / 1991 can be referred to.

[0055] plan 1

[0056]

[0057] wherein Y represents a chlorine atom or a hydroxyl group; and R 1 , R 2 , R 3 , R 4 and X are as defined in formula (I).

[0058]A compound of formula (I) can be synthesized by reacting a compound of formula (II) with a reagent represented by formula (III) in the absence of a solvent or in the presence of a suitable solvent. When Y represents a chlorine atom, the compound of formula (I) can be synthesized by reacting in the presence of a suitable base, such as an organic amine such as triethylamine or pyridine, or an inorganic base such as sodium carbonate, potassium carbonate or sodium hydride . When Y represents a hydroxyl group, the compound of formula (...

Embodiment 1

[0115] Example 1: 2-ethyl-3-methyl-4-cyclopropanecarbonyloxy-6,7-difluoroquinoline (compound 1) and 2- Ethyl-3-methyl-4-cyclopropanecarbonyloxy-5,6-difluoroquinoline (compound 2)

[0116] 3,4-Difluoroaniline (3.18 g) and 3.9 g ethyl 2-methyl-2-propanoyl acetate were refluxed in toluene (50 ml) in the presence of 0.3 ml boron trifluoride etherate for 3 hours. The resulting reaction mixture was washed with saturated sodium bicarbonate solution and saturated brine and dried over anhydrous sodium sulfate, and the solvent was evaporated off. The resulting intermediate was refluxed in diphenyl ether for 30 minutes and left to cool. The precipitate was then collected by filtration under reduced pressure to obtain 1.9 g of 2-ethyl-3-methyl-4-hydroxyl-6,7-difluoroquinoline and 2-ethyl-3-methyl-4-hydroxyl-5 , a mixture of 6-difluoroquinolines. 60% Sodium hydride (20 mg) was suspended in 2 ml of dimethylformamide. Alternatively, a mixture of 2-ethyl-3-methyl-4-hydroxy-6,7-difluoro...

Embodiment 2

[0120] Example 2: 2-ethyl-3-methyl-4-acetoxy-6,7-difluoroquinoline (compound 3)

[0121]2-Ethyl-3-methyl-4-cyclopropanecarbonyloxy-6,7-difluoroquinoline (5.5 g), prepared as described in Example 1, was dissolved in 50 ml of methanol. A solution of 2.5 g of sodium hydroxide in 50 ml of water was added to the solution, and the mixture was stirred at 50°C for 3 hours. The resulting reaction solution was allowed to stand to cool, and then poured into 50 ml of water. The mixture was neutralized with 1N hydrochloric acid, and the precipitate was collected by filtration to obtain 5.1 g of 2-ethyl-3-methyl-4-hydroxy-6,7-difluoroquinoline. 60% sodium hydride (96 mg) was suspended in 20 ml tetrahydrofuran. In addition, 446 mg of 2-ethyl-3-methyl-4-hydroxy-6,7-difluoroquinoline (starting material 1) was suspended in 10 ml of tetrahydrofuran, and the suspension of starting material 1 was added dropwise to In the above sodium hydride suspension under ice cooling. The mixture was stir...

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Abstract

A mixed composition for controlling alien parasitic insects on mammals and birds which contains, as the active ingredients, a compound of the following general formula (I) or its salt and at least one compound selected from among pyrethroid insecticides. The composition has a high effect of controlling resistant harmful insects, shows an immediate action and yet is highly safe. (I) wherein R<1> represents optionally substituted alkyl, optionally substituted alkenyl, optionally substituted alkynyl, -O-R<5> (wherein R<5> represents optionally substituted alkyl, optionally substituted alkenyl, or optionally substituted alkynyl), or -S-R<5> (wherein R<5> is as defined above); R<2> represents optionally substituted alkyl; one of R<3> and R<4> represents hydrogen while the other represents fluorine, chlorine, bromine or -CF3; and X represents fluorine or chlorine.

Description

[Background of the invention] [0001] field of invention [0002] The present invention relates to mixed compositions for controlling harmful organisms parasitic on mammals and birds, ie ectoparasites, comprising halogen-substituted quinoline derivatives and synthetic pyrethroid insecticides. [0003] related technology [0004] Japanese Patent No. 2633377 discloses quinoline derivatives as insecticides for agricultural and horticultural purposes. On the other hand, for example, "Insecticide Handbook" 12th edition, published by the British Crop Protection Society in 2000, mentions that synthetic pyrethroid insecticides have control activity against ectoparasites. However, since these synthetic pyrethroid insecticides have been used for many years, some ectoparasites have acquired drug resistance, so the control of drug-resistant ectoparasites has become very difficult. Therefore, there is a need to develop drugs capable of controlling such drug-resistant ectoparasites. ...

Claims

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Application Information

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IPC IPC(8): A01N53/00A61K31/222A61K31/275A61K31/47A61K45/06A61P33/00A61P33/14A61P43/00
CPCA61K31/47A61K45/06A61K31/275A01N53/00A61K31/222A61P33/00A61P33/14A61P43/00A01N47/06A01N43/42A01N2300/00A61K2300/00
Inventor 尾山和彦
Owner MEIJI SEIKA KAISHA LTD
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