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Fused heterocyclic compound or salt thereof, agricultural and horticultural insecticide containing fused heterocyclic compound, and method for using agricultural and horticultural insecticide

A kind of technology of condensed heterocyclic ring and compound, applied in the field of agricultural and horticultural pesticides, can solve the problems such as the condensed heterocyclic compound of undisclosed pyridazine ring

Active Publication Date: 2015-11-11
NIHON NOHYAKU CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Condensed heterocyclic compounds containing pyridazine rings are not disclosed in this document

Method used

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  • Fused heterocyclic compound or salt thereof, agricultural and horticultural insecticide containing fused heterocyclic compound, and method for using agricultural and horticultural insecticide
  • Fused heterocyclic compound or salt thereof, agricultural and horticultural insecticide containing fused heterocyclic compound, and method for using agricultural and horticultural insecticide
  • Fused heterocyclic compound or salt thereof, agricultural and horticultural insecticide containing fused heterocyclic compound, and method for using agricultural and horticultural insecticide

Examples

Experimental program
Comparison scheme
Effect test

reference example 1

[0648] Reference Example 1. Production of N-methyl-3-amino-6-trifluoromethylpyridazine

[0649]

[0650] A mixture of 6-trifluoromethyl-3-hydroxypyridazine (11.5 g), thionyl chloride (12.5 g), and dimethylformamide (1 ml) synthesized according to the method described in WO / 2005 / 047279 was heated to reflux for 3 Hour. Ice water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was dissolved in tetrahydrofuran (5 ml), and added dropwise to methylamine (40% methanol solution, 16.2 g) under ice-cooling. After stirring overnight at room temperature, water was poured into the reaction mixture, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to column chromatography to obtain the target compound (3'-1) (5....

reference example 2

[0652] Reference example 2. Synthesis of N-methyl-3-amino-4-bromo-6-trifluoromethylpyridazine

[0653]

[0654] N-methyl-3-amino-6-trifluoromethylpyridazine (1.8 g) (3'-1), 3,5-dibromohydantoin (3.15 g) produced in Reference Example 1, The mixture of acetonitrile (10ml) was heated to reflux for 3 hours. A saturated sodium thiohydrogensulfate solution was poured into the reaction mixture, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to column chromatography to obtain the target compound (3') (0.9 g).

[0655] Physical properties: 1 H-NMR (CDCl 3 ): 7.70 (s, 1H), 5,41 (brs, 1H), 3,26 (d, 1H)

manufacture Embodiment 1-1

[0657] Production of 2-(2-fluoro-4-trifluoromethylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-C]pyridazine

[0658]

[0659] N-methyl-3-amino-4-bromo-6-trifluoromethylpyridazine (475 mg) (3′), 2-fluoro-4-trifluoromethylbenzamide ( A mixture of 500 mg) (2'), potassium tert-butoxide (311 mg), diphenylphosphinoferrocenepalladium dichloride (151 mg), toluene (5 ml) was heated at reflux under argon for 12 hours. Water was poured into the reaction mixture, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to column chromatography to obtain the target compound (I'-2) (0.16 g).

[0660] Physical properties: 1 H-NMR (CDCl 3 ): 8.21(s, 1H), 7.97(t, 1H), 7.72(d, 1H), 7.64(d, 1H), 4.12(d, 3H)

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Abstract

Given that damage caused by pests is still significant in agricultural and horticultural crop production, and the like, the present invention addresses the problem of developing and providing a novel agricultural and horticultural insecticide because of factors such as the prevalence of pests that are resistant to existing chemicals. Provided is a fused heterocyclic compound or salt thereof represented by general formula (I) {wherein: A1, A2 and A3 may be the same or different, and represent a nitrogen atom or a CH radical; R1 represents an alkyl group or the like; R2 represents a haloalkyl group or the like; R3 represents a hydrogen atom or the like; R4 represents a haloalkyl group or the like; R5 represents an alkyl group or the like; and m represents 0 or 2.} Further provided are: an agricultural and horticultural insecticide that uses the fused heterocyclic compound or a salt thereof as an active ingredient; and a method for using the agricultural and horticultural insecticide.

Description

Technical field [0001] The present invention relates to agricultural and horticultural pesticides using certain fused heterocyclic 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 fused heterocyclic compounds are useful as insecticides (for example, refer to Patent Documents 1 to 6). No condensed heterocyclic compounds containing pyridazine rings are disclosed in this document. [0003] existing technical documents [0004] patent documents [0005] Patent Document 1: Japanese Patent Application Publication No. 2009-280574 [0006] Patent Document 2: Japanese Patent Application Publication No. 2010-275301 [0007] Patent Document 3: Japanese Patent Application Publication No. 2011-79774 [0008] Patent Document 4: Japanese Patent Application Publication No. 2012-131780 [0009] Patent Document 5: ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D487/04A01N43/90A01P7/04A61K31/5025A61P33/14
CPCC07D487/04A01N43/90A61P33/14
Inventor 米村树深津浩介古谷敬诹访明之
Owner NIHON NOHYAKU CO LTD
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