Fused heterocyclic compounds and pest control agents

A technology of fused heterocycles and compounds, which is applied in the field of pest control agents and can solve the problems that fused heterocycles do not have any disclosures, etc.

Inactive Publication Date: 2021-04-13
NISSAN CHEM IND LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] Various condensed heterocyclic compounds are disclosed in Patent Documents 1 to 31, but there is nothing disclosed about the condensed heterocyclic compound of the present invention

Method used

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  • Fused heterocyclic compounds and pest control agents
  • Fused heterocyclic compounds and pest control agents
  • Fused heterocyclic compounds and pest control agents

Examples

Experimental program
Comparison scheme
Effect test

Embodiment

[0637] Hereinafter, the present invention will be described in more detail by giving examples of synthesis examples and test examples of the compounds of the present invention, but the present invention is not limited thereto.

[0638] The medium-pressure fractionation liquid chromatography used below was a medium-pressure fractionation device (YFLC-Wprep, manufactured by Yamazen Co., Ltd., flow rate 18 ml / min, silica gel 40 μm column).

[0639] In addition, the proton nuclear magnetic resonance spectrum described below (hereinafter referred to as 1 H-NMR) chemical shift values ​​using Me 4 Si (tetramethylsilane) was measured as a reference substance in a deuterated chloroform solvent at 300 MHz (model: JNM-ECX300 or JNM-ECP300, manufactured by JEOL).

[0640] 1 The symbols in the chemical shift value of H-NMR have the following meanings.

[0641] s: singlet, d: doublet, dd: double doublet, t: triplet, q: quartet, m: multiplet

Synthetic example 1

[0642] Synthesis Example 1: 2-[6-Chloro-3-(ethylthio)pyrazolo[1,5-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)-3H -Synthesis of imidazo[4,5-b]pyridine (Compound No.1-1-001b of the present invention)

[0643] Step 1: Synthesis of 6-chloro-N-[2-(methylamino)-5-(trifluoromethyl)pyridin-3-yl]pyrazolo[1,5-a]pyridine-2-carboxamide

[0644] At room temperature, to N 2 500mg of 6-chloropyrazolo[1,5-a]pyridine-2-carboxylic acid was sequentially added to a mixed solution of 584mg of methyl-5-(trifluoromethyl)pyridine-2,3-diamine and 5ml of pyridine , 975 mg of 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride and 31 mg of 4-dimethylaminopyridine. After the addition was complete, the mixture was stirred at room temperature for 18 hours. After completion of the reaction, 10 ml of water was added to the reaction mixture, and the precipitated solid was filtered off to obtain 500 mg of the target product. It was directly used in the subsequent step 2 without further purificati...

Synthetic example 2

[0651] Synthesis Example 2: 2-[6-Chloro-3-(ethylsulfonyl)pyrazolo[1,5-a]pyridin-2-yl]-3-methyl-6-(trifluoromethyl)- Synthesis of 3H-imidazo[4,5-b]pyridine (Compound No.1-1-001a of the present invention)

[0652] To a mixed solution of 200 mg of the present compound No. 1-1-001b obtained in Synthesis Example 1 and 5 ml of chloroform was added 184 mg of 65% by mass m-chloroperbenzoic acid (containing about 30% by mass of water) under ice cooling. After the addition was complete, the mixture was stirred at room temperature for 18 hours. After completion of the reaction, saturated aqueous sodium thiosulfate solution was added to the reaction mixture, followed by extraction with 10 ml of chloroform. The obtained organic layer was washed with 10 ml of a 1 mol / L (liter) sodium hydroxide aqueous solution, dehydrated and dried with anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The obtained residue was purified by medium pressure fractionation liq...

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Abstract

The present invention provides novel pest control agents, particularly insecticides or acaricides. A condensed heterocyclic compound represented by formula (1), its salt or their N-oxide. [Q represents the structures shown in Q1, Q2, etc., replaced by -S(O) n R 1 D represents the structure shown in D1 or D2, A 1 means N(A 1a ) etc., A 1a means C 1 ~C 6 Alkyl etc., A 4 Indicates nitrogen atom or C(R 4 ), A 5 Indicates nitrogen atom or C(R 5 ), R 1 means C 1 ~C 6 Alkyl etc., R 2 , R 5 and R 6 Each independently represents a hydrogen atom or C 1 ~C 6 Alkyl, R 3 , R 4 , Y1, Y2, Y3 and Y4 each independently represent a halogen atom, a halogenated (C 1 ~C 6 ) alkyl, etc., n represents an integer of 0, 1 or 2. ][Chem.1]

Description

technical field [0001] The present invention relates to novel condensed heterocyclic compounds and their salts, and pest control agents containing the compounds as active ingredients. Background technique [0002] Various condensed heterocyclic compounds are disclosed in Patent Documents 1 to 31, but there is nothing disclosed about the condensed heterocyclic compound of the present invention. In addition, the usefulness of the condensed heterocyclic compound of the present invention as a pest control agent, especially usefulness as an insecticide, acaricide, and internal or external parasite control agent for mammals, fish, or birds Sex is completely undisclosed. [0003] prior art literature [0004] patent documents [0005] Patent Document 1: International Publication No. 2016 / 005263 [0006] Patent Document 2: International Publication No. 2015 / 198859 [0007] Patent Document 3: International Publication No. 2015 / 133603 [0008] Patent Document 4: International Pu...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/04A01N25/00A01N43/90A01P7/02A01P7/04A61K31/437A61P33/02A61P33/04A61P33/06A61P33/10A61P33/12A61P33/14C07D519/00
CPCA01N25/00A01N43/90A61K31/437C07D471/04C07D519/00C07D487/04C07D513/04A61P33/02A61P33/04A61P33/06A61P33/10A61P33/12A61P33/14
Inventor 工藤隆生辻敬介能登健吉舞鹤幸裕松井洋人小林正树今仲穗高
Owner NISSAN CHEM IND LTD
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