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

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 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 or external parasite control agent for animals, and methods for using the same. In the formula, R1 represents a haloalkyl group, R2 represents a thienyl group, and R3 represents an alkylthioalkyl group.

Description

Technical field

[0001] The present invention relates to agricultural and horticultural insecticides or external or internal parasite control agents for animals containing imidazopyridazine compounds or salts thereof as active ingredients, and their use methods. 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). These documents do not specifically disclose a compound in which a pyridine ring having an oxime group and an imidazopyridazine ring are bonded.

[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 Publication No. 2017 / 065183

[0008] Patent Document 4: International...

Examples

preparation example Construction

[0050] Preparation method of process A

[0051] The compound represented by the general formula (2-1) can be obtained by combining a carboxylic acid compound represented by the general formula (2) prepared according to the method described in International Publication No. 2017 / 146221 in the presence of a base and an inert solvent. The compound represented by general formula (3) is produced by reacting with a condensing agent.

[0052] Examples of bases that can be used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, and potassium bicarbonate; acetates such as potassium acetate; triethylamine , diisopropylethylamine, 1,8-diazabicyclo[5.4.0]undec-7-ene and other tertiary amines; pyridine, 4-dimethylaminopyridine and other nitrogen-containing aromatic compounds, etc. , the amount used is usually within the range of 1-fold mole to 10-fold mole relative to the compound represented by...

reference example 1

[0179] The preparation method of reference example 1.N-methylthioethoxyphthalimide

[0180] [chemical formula 4]

[0181]

[0182] Diethyl azodicarboxylate ( 2.2M solution in toluene, 33.4 mL). After stirring at room temperature for 1 hour, it was concentrated. The residue was subjected to column chromatography to obtain the target N-methylthioethoxyphthalimide (15 g, yield: quantitative).

reference example 2

[0183] The preparation method of reference example 2.methylthioethoxylamine

[0184] [chemical formula 5]

[0185]

[0186] To a mixture of N-ethylthioethoxyphthalimide (15 g), chloroform (60 mL) was added hydrazine monohydrate (3 mL). After stirring at room temperature for 4 hours, the insoluble matter was removed by filtration through celite. After drying the filtrate with magnesium sulfate, it filtered again. The obtained filtrate was made into a 0.3M solution of methylthioethoxyamine and used for the reaction.

Technical field

[0001] The present invention relates to agricultural and horticultural insecticides or external or internal parasite control agents for animals containing imidazopyridazine compounds or salts thereof as active ingredients, and their use methods. 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). These documents do not specifically disclose a compound in which a pyridine ring having an oxime group and an imidazopyridazine ring are bonded.

[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 Publication No. 2017 / 065183

[0008] Patent Document 4: International...

Examples

preparation example Construction

[0050] Preparation method of process A

[0051] The compound represented by the general formula (2-1) can be obtained by combining a carboxylic acid compound represented by the general formula (2) prepared according to the method described in International Publication No. 2017 / 146221 in the presence of a base and an inert solvent. The compound represented by general formula (3) is produced by reacting with a condensing agent.

[0052] Examples of bases that can be used in this reaction include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, and potassium bicarbonate; acetates such as potassium acetate; triethylamine , diisopropylethylamine, 1,8-diazabicyclo[5.4.0]undec-7-ene and other tertiary amines; pyridine, 4-dimethylaminopyridine and other nitrogen-containing aromatic compounds, etc. , the amount used is usually within the range of 1-fold mole to 10-fold mole relative to the compound represented by...

reference example 1

[0179] The preparation method of reference example 1.N-methylthioethoxyphthalimide

[0180] [chemical formula 4]

[0181]

[0182] Diethyl azodicarboxylate ( 2.2M solution in toluene, 33.4 mL). After stirring at room temperature for 1 hour, it was concentrated. The residue was subjected to column chromatography to obtain the target N-methylthioethoxyphthalimide (15 g, yield: quantitative).

reference example 2

[0183] The preparation method of reference example 2.methylthioethoxylamine

[0184] [chemical formula 5]

[0185]

[0186] To a mixture of N-ethylthioethoxyphthalimide (15 g), chloroform (60 mL) was added hydrazine monohydrate (3 mL). After stirring at room temperature for 4 hours, the insoluble matter was removed by filtration through celite. After drying the filtrate with magnesium sulfate, it filtered again. The obtained filtrate was made into a 0.3M solution of methylthioethoxyamine and used for the reaction.

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