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Agricultural and horticultural insecticide or external or internal parasite control agent for animals, containing imidazopyridazine compound having substituted cyclopropane oxadiazole group or salt thereof as active ingredient, and method for using same

A technology of cyclopropane oxadiazolyl and imidazopyridazine, which is applied in the field of external or internal parasite control agents, and can solve the problems of unspecified disclosure of imidazopyridazine compounds, etc.

Pending Publication Date: 2022-05-13
NIHON NOHYAKU CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Certain types of imidazopyridazine compounds having a substituted cyclopropane oxadiazolyl group are not specifically disclosed in these documents

Method used

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  • Agricultural and horticultural insecticide or external or internal parasite control agent for animals, containing imidazopyridazine compound having substituted cyclopropane oxadiazole group or salt thereof as active ingredient, and method for using same
  • Agricultural and horticultural insecticide or external or internal parasite control agent for animals, containing imidazopyridazine compound having substituted cyclopropane oxadiazole group or salt thereof as active ingredient, and method for using same
  • Agricultural and horticultural insecticide or external or internal parasite control agent for animals, containing imidazopyridazine compound having substituted cyclopropane oxadiazole group or salt thereof as active ingredient, and method for using same

Examples

Experimental program
Comparison scheme
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preparation example Construction

[0044] Production method of process [A]

[0045] The amidoxime compound represented by the general formula (1-1) can be produced by reacting a nitrile compound represented by the general formula (1-2) with hydroxylamines in the presence of a base and an inert solvent.

[0046] As the base used in this reaction, for example, inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, and potassium bicarbonate; acetates such as sodium acetate and potassium acetate; Potassium butoxide, sodium methoxide, sodium ethoxide and other alkali metal alkoxides; triethylamine, diisopropylethylamine, 1,8-diazabicyclo[5.4.0]undec-7-ene and other tertiary Amines; nitrogen-containing aromatic compounds such as pyridine and dimethylaminopyridine, etc., are usually used in the range of 1 to 10 times the mole of the compound represented by the general formula (1-2). .

[0047] Examples of hydroxylamines used in this reaction include ...

preparation Embodiment 1

[0178] Preparation Example 1.3-(5-(ethylsulfonyl)-6-(3-methyl-6-pentafluoroethyl-3H-imidazo[4,5-c]pyridazin-2-yl)pyridine- Preparation method of 3-yl)-5-(1-trifluoromethylcyclopropyl)-1,2,4-oxadiazole (compound number 1-2)

[0179] [chemical formula 3]

[0180]

[0181] N'-hydroxy-6-(3-methyl-6-pentafluoroethyl-3H-imidazo[4,5-c]pyridazine- 2-yl)-5-(ethylsulfonyl)pyridine-3-carboxamidine (0.15 g) was dissolved in THF (tetrahydrofuran, 3 mL), triethylamine (0.10 g), 1-trifluoromethylcyclopropane were added Formyl chloride (0.067g), stirred at room temperature for 1 hour. The reaction solution was concentrated under reduced pressure. This was dissolved in acetic acid (1 mL), and the acetic acid solution was dissolved in toluene (2 mL), and stirred at 120° C. for 1 hour. Saturated aqueous sodium carbonate solution was added, followed by extraction with ethyl acetate. The organic layer was dried using anhydrous magnesium sulfate, and concentrated under reduced pressure. Th...

preparation example 1

[0185]

[0186] Mix and dissolve the above substances evenly to make an emulsion.

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Abstract

The technical problem of the present invention is to develop and provide a novel agricultural and horticultural insecticide in order to solve the problems that disasters caused by pests and the like are still large in agricultural and horticultural crop production, and pests resistant to existing drugs are generated, and the like. The invention also provides an agent for exterminating external parasites or internal parasites for animals. The above-mentioned problem is solved by an imidazopyridazine compound having a substituted cyclopropane oxadiazole group represented by general formula (1) or a salt thereof, an agricultural and horticultural insecticide containing the compound or the salt thereof as an active ingredient, an internal and external parasite control agent for animals, and methods for using the same. In the formula, R1 represents an alkyl group, R2a and R2b represent hydrogen atoms, and R3 represents a haloalkyl group.

Description

Technical field [0001] The present invention relates to agricultural and horticultural insecticides or external or internal parasite control agents for animals containing an imidazopyridazine compound having a substituted cyclopropaneoxadiazolyl group or a salt thereof as an active ingredient, and methods of using the same. Background technique [0002] Various compounds have been studied as agricultural and horticultural insecticides, and it has been reported that certain types of imidazopyridazine compounds can be used as insecticides (see, for example, Patent Documents 1 to 4). Certain types of imidazopyridazine compounds having substituted cyclopropaneoxadiazolyl groups are not specifically disclosed in these documents. [0003] existing technical documents [0004] patent documents [0005] Patent Document 1: International Publication No. 2014 / 142292 [0006] Patent Document 2: International Publication No. 2016 / 104746 [0007] Patent Document 3: International Publi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): A01N43/90A01P7/02A01P7/04A01P9/00A61K31/5025A61P33/00A61P33/10A61P33/14C07D487/04A01G13/00
CPCA01N43/90A61K31/5025A61P33/00A61P33/10A61P33/14C07D487/04A01G13/00A01P7/00A61K9/0053
Inventor 山内千明米村树
Owner NIHON NOHYAKU CO LTD
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