Condensed heterocyclic compound or salt thereof comprising nitrogen atom in cross-link, and agricultural pesticide containing said compound and method for using same

A technology of heterocyclic compounds and nitrogen atoms, applied in gardening methods, insecticides, nematicides, etc., can solve problems that have not been specifically disclosed

Active Publication Date: 2022-01-07
NIHON NOHYAKU CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

These documents do not specifically disclose compounds in which a pyridine ring having an oxime group is bonded to a condensed heterocyclic ring having a nitrogen atom in a crosslinking portion.

Method used

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  • Condensed heterocyclic compound or salt thereof comprising nitrogen atom in cross-link, and agricultural pesticide containing said compound and method for using same
  • Condensed heterocyclic compound or salt thereof comprising nitrogen atom in cross-link, and agricultural pesticide containing said compound and method for using same
  • Condensed heterocyclic compound or salt thereof comprising nitrogen atom in cross-link, and agricultural pesticide containing said compound and method for using same

Examples

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preparation example Construction

[0062] Preparation method of step [a]

[0063] The compound represented by the formula (1a) can be, and the compound represented by the formula (1-4) prepared in the preparation method 3 described later in the preparation method 3 is prepared in the presence of a base and an inert solvent. 4) The compound represented (NH) 2 Organ 3 Reaction and prepared.

[0064] As the base which can be used in this reaction, for example, an inorganic base such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium hydrogencarbonate can be mentioned; acetate such as potassium acetate; triethylamine , Diisopropylamine, 1,8-diazepine diprocyte [5.4.0] eclipanoamine such as 11 carbon-7-ene; pyridine, 4-dimethylaminopyridine and other nitrogen-containing aromatic compounds, etc. For its amount, it is usually used in the range of 1 x mole to 10 dimension relative to the compound represented by the formula (4).

[0065] As the inert solvent used i...

reference example 1

[0249] Reference Example 1. Preparation method of trifrofluoromethylpyrimidine-1-lysonium-1,6-diamine 2,4,6-trimethylsulfonate

[0250] [Chemical Formula 9]

[0251]

[0252]2,2,2-trifluoroacetic acid (4.4 g, 2.54 mmol, 2.9 mL) was added to a microwave tube having a magnetic stirrer, and then added (tert-butoxycarbonyl amino) 2, 4, 6- at 0 ° C. Trimethylbenzenesulfonate (1 g, 2.54 mmol). The reaction mixture was stirred at 0 ° C for 2 hours, and ice water was added, and the precipitate was recovered by filtration. Wash the moist filter cake with water, and dissolved in dichloromethane (5 mL), dried to sodium sulfate. The resulting solution was added dropwise to 6-trifluoromethylpyrimidine-4-amine (0.373 g, dichloromethane (5ml) (5ml) (5 ml) (5ml) (5ml) (5ml) (5ml) (5ml) (5ml) (5 ml) (5 ml) (5 ml) (5 ml) (5 ml) (5 ml) (5 ml) (5ml) (5ml) (5ml) (5ml) (5ml) (5ml) (5ml) (5ml) (5ml) (5ml) (5ml) (5ml) (5ml) (5ml). )middle. After 1 hour after this temperature and after one night at room...

reference example 2

[0253] Reference Example 2.2- (3-ethylsulfonyl-5-bromo-2-pyridyl) -7-trifluoromethyl-[1,2,4] triazole [1,5-C] pyrimidine preparation method

[0254] [Chemical Formula 10]

[0255]

[0256] 4-trifluoroamine-1-lyson-1,6-diamine 2,4,6-trimethylsulfonate (0.3 g, 0.791 mmol), 3-ethylsulfonyl-5-bromine Pyridin-2-carboxylic acid (0.284 g, 1.18 mmol) and 3- (ethylene aminomethylene) -N, N-dimethyl-propane-1-amine hydrochloride (0.18 g, 0.94 mmol) Dissolved in pyridine (2 mL), heated at 120 ° C for 3 hours. Then, the reaction mixture was injected into water, and the aqueous layer was extracted 3 times using EtOAc (ethyl acetate). Wash the combined organic layers in times of water and brine, use anhydrous NA 2 SO 4 (Sodium sulfate) was dried and filtered and concentrated under reduced pressure. The crude product was washed with diethyl ether and filtered to give a target product as a white powder (90 mg, 33%).

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Abstract

The present invention addresses the problem of developing and providing a compound or salt thereof, and a novel agricultural pesticide containing said compound or salt thereof, and of providing a chemical for controlling external parasites or internal parasites of animals. Said problem is solved by: a compound in which a pyridine ring comprising an oxime group represented by general formula (1) is bonded to a condensed heterocyclic compound comprising a nitrogen atom in a cross-link, or a salt thereof; an agricultural pesticide and internal or external parasite control agent, for animals, that utilize said compound or salt as an active ingredient; and a method for using the same.

Description

Technical field [0001] The present invention relates to an agricultural horticulture of a condensed heterocyclic compound having a nitrogen atom with a crosslinked portion, or a salt as an agricultural horticulture with an active ingredient. Background technique [0002] To date, various compounds of the pesticide for agricultural gardening have been studied, and there is a report that certain types of condensation heterocyclic compounds can be used as insecticides (e.g., refer to Patent Documents 1 to 11). These documents have not specifically disclosed compounds having a gyridine ring having a hydrazine and a condensed heterocyclic ring bonded to the crosslinking portion. [0003] Prior art literature [0004] Patent literature [0005] Patent Document 1: Japanese Laid-Open No. 2009-280574 [0006] Patent Document 2: Japanese Laid-Open 2010-275301 [0007] Patent Document 3: Japanese Laid-Open 2011-79774 [0008] Patent Document 4: Japanese Laid-Open 2012-131780 [0009] Patent...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/04C07D487/04A01N43/90A01P7/04A61K31/519A61K31/444A61P33/14A01G13/00A01G7/06C09K17/14C09K101/00
CPCC07D471/04C07D487/04A01N43/90A61P33/14A01G13/00A01G7/06C09K17/14C09K2101/00A01N47/34A01N47/12A61P33/10A01P7/04A01P5/00A01P1/00A01P7/02
Inventor 佐野勇介米村树
Owner NIHON NOHYAKU CO LTD
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